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stringclasses 84
values | solvent2
stringclasses 40
values | reagent1
stringclasses 222
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stringclasses 94
values | dataset
stringclasses 1
value |
|---|---|---|---|---|---|---|---|
US20090239848A1 | O=[N+]([O-])c1ccc(N2CCOCC2)cc1>>Nc1ccc(N2CCOCC2)cc1 | [Zn] | C1CCOC1 | O | CO | [Cl-].[NH4+] | train |
US20050261337A1 | CN(C)C=O.Clc1ccc2cc(Cc3ccccc3)c(I)nc2c1>>O=Cc1nc2cc(Cl)ccc2cc1Cc1ccccc1 | null | C1CCOC1 | null | CC(C)[Mg]Cl | null | train |
US20100120798A1 | CC(C)(C)OC(=O)NCC(=O)O.Cn1cc(-c2cccc(C3(CN)CCN(C(=O)OC(C)(C)C)CC3)c2)cn1>>Cn1cc(-c2cccc(C3(CNC(=O)CNC(=O)OC(C)(C)C)CCN(C(=O)OC(C)(C)C)CC3)c2)cn1 | null | CN(C)C=O | null | CCN(C(C)C)C(C)C | CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F | train |
US05554607 | CCOC(=O)CNC.Cc1ccc(N=C=S)cc1Cl>>Cc1ccc(N2C(=O)CN(C)C2=S)cc1Cl | null | ClC(Cl)Cl | null | CCN(CC)CC | Cl | train |
US20090118284A1 | C1=C(c2ccc(-c3ncccn3)cn2)CCNC1.O=C(Cl)CCl>>O=C(CCl)N1CC=C(c2ccc(-c3ncccn3)cn2)CC1 | null | ClCCl | null | CCN(CC)CC | O=C([O-])O.[Na+] | train |
US20120208874A1 | CC#CCBr.CCCc1cc2c(cc1O)OCO2>>CC#CCOc1cc2c(cc1CCC)OCO2 | null | CC(C)=O | null | O=C([O-])[O-].[K+].[K+] | null | train |
US20080004271A1 | CC(C)(C)OC(=O)N1CC[C@@H](N)C1.CS(=O)c1nc(-c2ccc(Cl)c(Cl)c2)c2c(N)c(C(N)=O)sc2n1>>CC(C)(C)OC(=O)N1CC[C@@H](Nc2nc(-c3ccc(Cl)c(Cl)c3)c3c(N)c(C(N)=O)sc3n2)C1 | null | C1CCOC1 | null | null | null | train |
US20110313172A1 | CCOC(=O)C(=O)CC(=O)c1cccc(Cl)c1.NO>>CCOC(=O)c1cc(-c2cccc(Cl)c2)on1 | null | CCO | null | Cl | O | train |
US20080021071A1 | CNCC(O)CO.O=Cc1ccc(-c2ccc(N3C[C@H](Cn4ccnn4)OC3=O)cc2F)cn1>>CN(Cc1ccc(-c2ccc(N3C[C@H](Cn4ccnn4)OC3=O)cc2F)cn1)CC(O)CO | null | C1CCOC1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+] | null | train |
US07705042B2 | CC1CCN(c2cc(N3CCN(C(=O)OC(C)(C)C)CC3)ccc2[N+](=O)[O-])CC1.N#Cc1ccc(C(=O)O)o1>>CC1CCN(c2cc(N3CCN(C(=O)OC(C)(C)C)CC3)ccc2NC(=O)c2ccc(C#N)o2)CC1 | [Pd] | null | null | CCN(C(C)C)C(C)C | O=C(Cl)C(=O)Cl | train |
US06329381B1 | CO.Nc1nc(OCCCO)nc2c1nc(Br)n2Cc1ccccc1>>COc1nc2c(N)nc(OCCCO)nc2n1Cc1ccccc1 | null | CO | null | C[O-].[Na+] | null | train |
US20090275606A1 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.O=c1c(F)c2c([nH]c(=O)n2-c2ccc(Br)cc2F)c2n1CCC2>>CC(C)(C)OC(=O)n1c(=O)n(-c2ccc(Br)cc2F)c2cc(=O)n3c(c21)CCC3 | null | C1CCOC1 | CN(C)C=O | [H-].[Na+] | null | train |
US20100298324A1 | Cc1c(N)cc(C(=O)O)cc1[N+](=O)[O-].O=N[O-]>>Cc1c(O)cc(C(=O)O)cc1[N+](=O)[O-] | null | O | null | O=S(=O)(O)O | null | train |
US06251912B1 | CC#CC(=O)Nc1ccc(N=CN(C)C)c(C#N)c1.Nc1cccc(Br)c1>>CC#CC(=O)Nc1ccc2ncnc(Nc3cccc(Br)c3)c2c1 | null | CC(=O)O | null | null | null | train |
US20140336185A1 | CC(C)(C)OC(=O)CN(Cc1ccc(C#N)cc1)C(=O)c1ccc([N+](=O)[O-])cc1.NO>>CC(C)(C)OC(=O)CN(Cc1ccc(C(=N)NO)cc1)C(=O)c1ccc([N+](=O)[O-])cc1 | null | CN(C)C=O | null | Cl | O=C([O-])O.[Na+] | train |
US20030144360A1 | CC(C)(Cl)CCC(C)(C)Cl.Ic1ccccc1>>CC1(C)CCC(C)(C)c2cc(I)ccc21 | null | CCCCCC | null | [Al+3].[Cl-].[Cl-].[Cl-] | null | train |
US20150175584A1 | CC1(C)OCCC1N.COc1ccc2c(Cl)ncnc2c1OC>>COc1ccc2c(NC3CCOC3(C)C)ncnc2c1OC | null | CN(C)C=O | null | CCN(C(C)C)C(C)C | null | train |
US20090181965A1 | COc1cc(Nc2nc3c(s2)CCCC3c2ccccc2)ccc1C(N)=O>>COc1cc(Nc2nc3c(s2)CCCC3c2ccccc2)ccc1C#N | null | C1COCCO1 | null | O=C(OC(=O)C(F)(F)F)C(F)(F)F | c1ccncc1 | train |
US20020123497A1 | CC(C)(C)OC(=O)N1CCN(Cc2cc(O[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)ccc2Cl)C(=O)C1>>CC(C)(C)[Si](Oc1ccc(Cl)c(CN2CCNCC2=O)c1)(c1ccccc1)c1ccccc1 | null | ClCCl | null | O=C(O)C(F)(F)F | O=C([O-])O.[Na+] | train |
US20140018321A1 | CC(C)(C)OP(=O)(OCc1cccc(C(=O)O)c1)OC(C)(C)C.CC(C)(O)c1cn(-c2ccc(-c3cc(F)c(CO)c(S(C)(=O)=O)c3)cc2F)c(C(C)(C)c2c(Cl)cccc2Cl)n1>>CC(C)(C)OP(=O)(OCc1cccc(C(=O)OCc2ccc(-c3ccc(-n4cc(C(C)(C)O)nc4C(C)(C)c4c(Cl)cccc4Cl)c(F)c3)cc2F)c1)OC(C)(C)C | CN(C)c1ccncc1 | ClCCl | null | C(=NC1CCCCC1)=NC1CCCCC1 | null | train |
US20090162283A1 | CC(=O)c1ccc(C=O)cc1.Cc1ccc(S(=O)(=O)CN=C=O)cc1>>CC(=O)c1ccc(-c2cnco2)cc1 | null | CO | null | O | O=C([O-])[O-].[K+].[K+] | train |
US05929094 | CC(=O)O.COc1cc([N+](=O)[O-])cc(Br)c1N>>COc1cc([N+](=O)[O-])cc(Br)c1NC(C)=O | null | CC(=O)O | null | CC(=O)OC(C)=O | null | train |
US20020103229A1 | O=C(N[C@@H]1c2ccccc2C[C@@H]1O)c1cccc(-c2nn(C3CCCCO3)c3ccc(-c4ncn(C(c5ccccc5)(c5ccccc5)c5ccccc5)n4)cc23)c1>>O=C(N[C@@H]1c2ccccc2C[C@@H]1O)c1cccc(-c2n[nH]c3ccc(-c4ncn[nH]4)cc23)c1 | null | C1COCCO1 | null | Cl | O=C([O-])O.[Na+] | train |
US20150322056A1 | CC(C)Oc1cc(Cl)cnn1.Ic1cc[nH]n1>>CC(C)Oc1cc(-n2ccc(I)n2)cnn1 | null | CCOC(C)=O | CN(C)C=O | CC(C)(C)[O-].[K+] | null | train |
US04864021 | ClCc1ccccc1Cl.O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1F>>O=c1[nH]c(=O)n([C@H]2C[C@H](OCc3ccccc3Cl)[C@@H](CO)O2)cc1F | null | C1COCCO1 | O | [K+].[OH-] | null | train |
US20160024095A1 | CCC(=O)Nc1cn2ccncc2n1>>CCC(=O)Nc1cn2c(n1)CNCC2 | O=[Pt]=O | CO | null | null | null | train |
US07375087B2 | C=CCC(=O)O.CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(C)C)c2Cc2ccc(Br)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O>>CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(C)C)c2Cc2ccc(/C=C/CC(=O)O)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | null | CC#N | null | CCN(CC)CC | Cc1ccccc1P(c1ccccc1C)c1ccccc1C | train |
US20080269268A1 | O=C1CCC(=O)N1Cl.O=[N+]([O-])c1ccc(Nc2ccnc3[nH]ccc23)c(F)c1>>O=[N+]([O-])c1ccc(Nc2ccnc3[nH]cc(Cl)c23)c(F)c1 | null | C1CCOC1 | null | O=C([O-])O.[Na+] | null | train |
US05302743 | COC(=O)[C@@H](N)Cc1ccccc1.O=CN[C@H]1CC(=O)OC1=O>>COC(=O)[C@H](Cc1ccccc1)NC(=O)C[C@H](NC=O)C(=O)O | null | ClCCl | null | Cl | CC(=O)[O-].[Na+] | train |
US05149703 | O=C1CCOc2ccc(OCc3ccccc3)cc21.O=Cc1cccc(C(=O)O)c1>>O=C(O)c1cccc(C=C2COc3ccc(OCc4ccccc4)cc3C2=O)c1 | null | CO | O | CC(=O)O | [Na+].[OH-] | train |
US05861395 | N.NS(=O)(=O)N=C(Oc1ccccc1)N1CCC(CC(=O)N2CCN(C3c4ccc(Cl)cc4CCc4cc(Br)cnc43)CC2)CC1>>N=C(NS(N)(=O)=O)N1CCC(CC(=O)N2CCN(C3c4ccc(Cl)cc4CCc4cc(Br)cnc43)CC2)CC1 | null | C1CCOC1 | null | null | null | train |
US20100305091A1 | Brc1cnc2c(Br)cnn2c1.OB(O)c1cccnc1>>Brc1cnn2cc(-c3cccnc3)cnc12 | null | CN(C)C=O | null | O=C([O-])O.[Na+] | null | train |
US20160145245A1 | CN[C@H](CN1CC[C@H](OCCOCCOCCOC(F)(F)F)C1)c1ccccc1.O=C(O)Cc1ccc(Cl)c(Cl)c1>>CN(C(=O)Cc1ccc(Cl)c(Cl)c1)[C@H](CN1CC[C@H](OCCOCCOCCOC(F)(F)F)C1)c1ccccc1 | null | CC#N | null | CCN(C(C)C)C(C)C | CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F | train |
US20070161617A1 | CC(C)(C)OC(=O)N1CCNCC1.COC(=O)c1c(F)ccc(CBr)c1F>>COC(=O)c1c(F)ccc(CN2CCN(C(=O)OC(C)(C)C)CC2)c1F | null | CCOC(C)=O | CN(C)C=O | O=C([O-])[O-].[K+].[K+] | null | train |
US20140194431A1 | CC(N(CCO)C(=O)c1nc(CC2(c3ccc(Cl)cc3)CCCC2)nc(O)c1OCc1ccccc1)C(F)(F)F>>CC(N1CCn2c(CC3(c4ccc(Cl)cc4)CCCC3)nc(=O)c(OCc3ccccc3)c2C1=O)C(F)(F)F | null | ClCCl | null | CC(C)OC(=O)N=NC(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | train |
US05153210 | CC(=O)CCl.CC1=C(c2ccc(O)cc2)CCC(=O)N1>>CC(=O)COc1ccc(C2=C(C)NC(=O)CC2)cc1 | null | CC(C)=O | null | [I-].[K+] | null | train |
US20130261106A1 | CC(C)Oc1cc(-n2cncn2)ccc1[N+](=O)[O-]>>CC(C)Oc1cc(-n2cncn2)ccc1N | [Pd] | CO | null | O=C[O-].[NH4+] | null | train |
US20120225854A1 | CCOC(=O)[C@H](Cc1cccnc1OC)N=C(c1ccccc1)c1ccccc1>>CCOC(=O)[C@@H](N)Cc1cccnc1OC | null | C1CCOC1 | null | Cl | null | train |
US20150126485A1 | CCOC(=O)c1cc(C(=O)Nc2ccc(OC(F)(F)F)cc2)cnc1Cl.O[C@@H]1CCNC1>>CCOC(=O)c1cc(C(=O)Nc2ccc(OC(F)(F)F)cc2)cnc1N1CC[C@@H](O)C1 | null | CC(C)O | null | CCN(C(C)C)C(C)C | null | train |
US20050209253A1 | CCOC(=O)C1CCNCC1.Cc1nc(Cl)c2c(n1)N(c1c(C)cc(Br)cc1C)C(=O)C2C>>CCOC(=O)C1CCN(c2nc(C)nc3c2C(C)C(=O)N3c2c(C)cc(Br)cc2C)CC1 | null | CCO | null | CCN(C(C)C)C(C)C | null | train |
US20150307497A1 | CC(C)(C)OC(=O)N1CCC(CN2Cc3cccc(O[C@@H]4CCCC[C@H]4O)c3C2=O)CC1>>O=C1c2c(cccc2O[C@@H]2CCCC[C@H]2O)CN1CC1CCNCC1 | null | CCOC(C)=O | null | Cl | null | train |
US03939159 | COc1ccc(-n2cccc2)c([N+](=O)[O-])c1>>COc1ccc(-n2cccc2)c(N)c1 | null | O | null | C1CCOC1 | null | train |
US06821988B2 | CCOc1cc2ncc(C#N)c(Nc3ccc(F)c(Cl)c3)c2cc1NC(=O)C=CCBr.CN(C)C=O.O[C@@H]1CCNC1>>COc1cc2ncc(C#N)c(Nc3ccc(F)c(Cl)c3)c2cc1NC(=O)CC(CN1CCC(O)C1)N1CCC(O)C1 | null | CN(C)C=O | null | O=C([O-])O.[Na+] | null | train |
US20100130492A1 | C1COCCN1.CNc1ncc(-c2nc(N3CCOCC3)c3nc(Cl)n(CC4CCOC4)c3n2)cn1>>CNc1ncc(-c2nc(N3CCOCC3)c3nc(N4CCOCC4)n(CC4CCOC4)c3n2)cn1 | null | CS(C)=O | null | null | null | train |
US20150080588A1 | CO[C@@H]1COCC[C@@H]1N[C@@H]1C[C@H]2OCC[C@@]2(C(=O)N2CCc3ncc(C(F)(F)F)cc3C2)C1.O=C(O)CCC(=O)O>>CO[C@@H]1COCC[C@@H]1N[C@@H]1C[C@H]2OCC[C@@]2(C(=O)N2CCc3ncc(C(F)(F)F)cc3C2)C1.O=C(O)CCC(=O)O | null | CO | null | C | null | train |
US05563163 | O=C(O)c1ccncc1.O=C1c2ccccc2S(=O)(=O)N1CBr>>O=C(OCN1C(=O)c2ccccc2S1(=O)=O)c1ccncc1 | null | Cc1ccccc1C | null | CCN(CC)CC | null | train |
US20120115813A1 | CCI.O=Cc1ccc(F)c(O)c1O>>CCOc1c(F)ccc(C=O)c1O | null | CS(C)=O | null | Cl | null | train |
US20090069297A1 | Nc1ccc(Oc2ccnc3cc(Br)cnc23)cc1>>Nc1ccc(Oc2ccnc3c2NCCC3)cc1 | [Pd] | CCOC(C)=O | CO | [H][H] | null | train |
US20120077799A1 | Nc1ncc(F)cc1-c1ccc(OC2CCCCC2)cc1.O=S(=O)(Cl)CCCl>>O=S1(=O)CCN2C=C(F)C=C(c3ccc(OC4CCCCC4)cc3)C2=N1 | null | C1CCOC1 | null | [H-].[Na+] | null | train |
US20070249589A1 | CC1(C)OC[C@@H](CN2CCN(C(=O)/C=C/c3ccc(Cl)c(Cl)c3)CCC2=O)O1>>O=C(/C=C/c1ccc(Cl)c(Cl)c1)N1CCC(=O)N(C[C@@H](O)CO)CC1 | null | CO | O | Cl | null | train |
US20070149519A1 | COc1cc2ncn(-c3cc(OCc4ccccc4S(C)(=O)=O)c(C(N)=O)s3)c2cc1OC>>COc1cc2ncn(-c3cc(OCc4ccccc4S(C)(=O)=O)c(C#N)s3)c2cc1OC | null | CO | CS(C)=O | null | null | train |
US20040092498A1 | CC(C)(C)OC(=O)CBr.O=C1NCCO1>>CC(C)(C)OC(=O)CN1CCOC1=O | null | C1CCOC1 | CCOC(C)=O | O | [H-].[Na+] | train |
US05922716 | CCOC(=O)CC1(C)C=CC(Cl)=C2C=c3[nH]c(=O)c(=O)[nH]c3=C21>>CC1(CC(=O)O)C=CC(Cl)=C2C=c3[nH]c(=O)c(=O)[nH]c3=C21 | null | [Na+] | [OH-] | C1COCCO1 | Cl | train |
US20160113928A1 | Cn1nccc1-c1nnc(N2CCC(N)CC2)c2ccccc12.O=Cc1ccc(F)cc1C(F)(F)F>>Cn1nccc1-c1nnc(N2CCC(NCc3ccc(F)cc3C(F)(F)F)CC2)c2ccccc12 | [Pd] | CO | null | null | null | train |
US04555572 | COc1ccc(COc2ccc([N+](=O)[O-])cc2)cc1>>COc1ccc(COc2ccc(N)cc2)cc1 | [Ni] | null | null | null | null | train |
US20130102785A1 | CC(C)=O.C[Si](C)(C)c1cc(Br)c(-c2sc([Si](C)(C)C)cc2Br)s1.O=C=O>>C[Si](C)(C)c1cc2c(s1)-c1sc([Si](C)(C)C)cc1C(=O)C2=O | null | C1CCOC1 | null | [Li]CCCC | [Cl-].[NH4+] | train |
US04540818 | O=C(c1cccc([N+](=O)[O-])c1)c1ccc(Cl)c([N+](=O)[O-])c1>>Nc1cccc(Cc2cccc(N)c2)c1 | [Pd] | CC(C)O | null | CCO | [H][H] | train |
US05346904 | COc1ccc([C@@H]2CN(C)CC[C@@H]2NC(=O)c2ccc(C)c(NS(=O)(=O)c3ccc(C)cc3)c2)cc1OC>>COc1cc2c(cc1OC)[C@@H]1CN(C)CC[C@@H]1N=C2c1ccc(C)c(NS(=O)(=O)c2ccc(C)cc2)c1 | null | O=P(Cl)(Cl)Cl | null | null | null | train |
US05461036 | CC(=O)OC(C)=O.CCCCCCCCCCCCCC[C@@H](O)C(=O)O>>CCCCCCCCCCCCCC[C@@H](OC(C)=O)C(=O)O | null | c1ccncc1 | null | CCOC(C)=O | O | train |
US20110152273A1 | CB1OB(C)OB(C)O1.Cc1cccc(Nc2nc(N[C@@H]3CCCC[C@@H]3NC(=O)OC(C)(C)C)c(Br)c3c2C(=O)NC3)c1>>Cc1cccc(Nc2nc(N[C@@H]3CCCC[C@@H]3NC(=O)OC(C)(C)C)c(C)c3c2C(=O)NC3)c1 | Cl[Pd]Cl | C1COCCO1 | O | O=C([O-])[O-].[K+].[K+] | null | train |
US20150119362A1 | OC1CCCC1.[O-][n+]1c(Cl)cc(Cl)c2c1CCC2>>[O-][n+]1c(OC2CCCC2)cc(Cl)c2c1CCC2 | null | CN1CCCC1=O | ClCCl | CC(C)(C)[O-].[K+] | null | train |
US20120214803A1 | CNS(=O)(=O)Cl.Nc1c(C(=O)c2ccc(F)c(F)c2)ccc2cccnc12>>CN1C(c2ccc(F)c(F)c2)c2ccc3cccnc3c2NS1(=O)=O | null | c1ccncc1 | null | [BH4-].[Na+] | null | train |
US20120190677A1 | CS(N)(=O)=O.Cc1ccc(N2CCOCC2)cc1C1CC(C)(C)c2cc(C(=O)O)ccc2N1>>Cc1ccc(N2CCOCC2)cc1C1CC(C)(C)c2cc(C(=O)NS(C)(=O)=O)ccc2N1 | null | CN(C)C=O | O | O=C(n1ccnc1)n1ccnc1 | [H-].[Na+] | train |
US04362728 | CN=C=S.NCCSCc1csc(NC(N)=NCC(F)(F)F)n1>>CNC(=S)NCCSCc1csc(NC(N)=NCC(F)(F)F)n1 | null | CO | null | null | null | train |
US20060173048A1 | CS(=O)(=O)OC1CCCC1.Clc1ccc(-c2[nH]c(-c3c(Cl)cccc3Cl)nc2-c2ccncc2)cc1>>Clc1ccc(-c2c(-c3ccncc3)nc(-c3c(Cl)cccc3Cl)n2C2CCCC2)cc1 | null | CN(C)C=O | null | CCOC(C)=O | [H-].[Na+] | train |
US20160244448A1 | C=Cc1cc(Nc2cccnc2)c(CNc2c(F)c(OC)cc(OC)c2F)cn1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>C=Cc1cc2c(cn1)CN(c1c(F)c(OC)cc(OC)c1F)C(=O)N2c1cccnc1 | null | C1CCOC1 | null | CCN(C(C)C)C(C)C | null | train |
US20120232056A1 | COC(=O)c1cc([N+](=O)[O-])c(F)cc1OC.COc1ccc(CN)cc1>>COC(=O)c1cc([N+](=O)[O-])c(NCc2ccc(OC)cc2)cc1OC | null | CN(C)C=O | O | CCN(C(C)C)C(C)C | null | train |
US20070072847A1 | O=S1(=O)CCC(N2CCN(Cc3ccccc3)CC2)CC1>>O=S1(=O)CCC(N2CCNCC2)CC1 | [Pd] | CO | null | [H][H] | null | train |
US04708955 | CC(C)(C)C(=O)OCI.CC/C=C\C1=C(C(=O)O)N2C(=O)C(NC(=O)/C(=N\OC)c3csc(N)n3)[C@H]2SC1>>CC/C=C\C1=C(C(=O)OCOC(=O)C(C)(C)C)N2C(=O)C(NC(=O)/C(=N\OC)c3csc(N)n3)[C@H]2SC1 | null | CCOC(C)=O | CN(C)C=O | O=C([O-])[O-].[K+].[K+] | null | train |
US04544758 | CC(=CCCl)CCC=C(C)CCCC(C)C.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>[Cl-].c1ccc([PH+](c2ccccc2)c2ccccc2)cc1 | null | Cc1ccccc1 | null | CCCCCC | null | train |
US20060270713A1 | CC(C)(C)OC(=O)N1CC[C@H](NCC2CCOC2)C1.O=Cc1ccccc1C(F)(F)F>>CC(C)(C)OC(=O)N1CC[C@H](N(Cc2ccccc2C(F)(F)F)CC2CCOC2)C1 | null | CC(Cl)Cl | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+] | null | train |
US05786379 | COC(=O)c1ccc(CSc2ccc(OC)c(C34CC5CC(CC(C5)C3)C4)c2)cc1.O=C(OO)c1cccc(Cl)c1>>COC(=O)c1ccc(CS(=O)c2ccc(OC)c(C34CC5CC(CC(C5)C3)C4)c2)cc1 | null | O | null | ClCCl | null | train |
US20050272672A1 | BrC(Br)(Br)Br.OCCc1cccc(-c2ccco2)c1>>BrCCc1cccc(-c2ccco2)c1 | null | ClCCl | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | train |
US20070293530A1 | CCOC(=O)CCCCC(=O)Nc1cccc2cccnc12>>O=C(CCCCCO)Nc1cccc2cccnc12 | null | C1CCOC1 | null | null | null | train |
US20160024072A1 | CC#N.CCOC(=O)CBr.O=c1nc(Cl)n(Cc2ccc(Cl)cc2)cc1O>>CCOC(=O)COCc1cn(Cc2ccc(Cl)cc2)c(Cl)nc1=O | null | CC(=O)N(C)C | O | O=C([O-])[O-].[K+].[K+] | null | train |
US20050148646A1 | N#Cc1ccc(-c2ccc(O)c(-c3nc4cc(C#N)ccc4[nH]3)c2)cc1.N#Cc1cccc(-c2ccc(O)c(C=O)c2)c1>>N#Cc1cccc(-c2ccc(O)c(-c3nc4cc(C#N)ccc4[nH]3)c2)c1 | null | CCO | null | null | null | train |
US20110070171A1 | CC(C)(C)C1(C(=O)O)CCCCC1.NC1CC1>>CC(C)(C)C1(C(=O)NC2CC2)CCCCC1 | null | ClCCl | null | CCN(CC)CC | O=S(Cl)Cl | train |
US06441017B1 | CC(C)(C)[Si](Oc1ccc2cccc(N3CC[C@H](NC(=S)Cc4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)cn4)C3=O)c2c1)(c1ccccc1)c1ccccc1>>CC(C)(C)[Si](Oc1ccc2cccc(N3CC[C@H](NCCc4cn(C(c5ccccc5)(c5ccccc5)c5ccccc5)cn4)C3=O)c2c1)(c1ccccc1)c1ccccc1 | [Ni] | CCO | CO | null | null | train |
US20160052940A1 | FC1(F)CCNC1.Nc1ncc(-c2cc(C3CC(=O)C3)nc(Cl)n2)cc1OC(F)F>>Nc1ncc(-c2cc(C3CC(=O)C3)nc(N3CCC(F)(F)C3)n2)cc1OC(F)F | null | CS(C)=O | null | Cl | O=C([O-])[O-].[K+].[K+] | train |
US06667412B1 | CC(C)C(C#N)(CCC(=O)O)c1ccccc1>>CC(C)C(C#N)(CCCO)c1ccccc1 | null | CO | null | C1CCOC1 | O=C([O-])O.[Na+] | train |
US20090099161A1 | COCCc1nc2cnc3ccc(C=CC(=O)N(C)C)cc3c2n1CCCN1CCCC1=O>>COCCc1nc2cnc3ccc(CCC(=O)N(C)C)cc3c2n1CCCN1CCCC1=O | [Pd] | CO | null | null | null | train |
US20120094964A1 | COC(=O)c1cccc(S(=O)(=O)Cl)c1.Nc1ncc(C(F)(F)F)cc1Cl>>COC(=O)c1cccc(S(=O)(=O)Nc2ncc(C(F)(F)F)cc2Cl)c1 | null | C1CCOC1 | null | Cl | [H-].[Na+] | train |
US20040127492A1 | COC(=O)c1c2c(nn1CCCNC(=O)OC(C)(C)C)-c1cc(-c3cccc([N+](=O)[O-])c3)c(OC)cc1CC2>>COc1cc2c(cc1-c1cccc([N+](=O)[O-])c1)-c1nn3c(c1CC2)C(=O)NCCC3 | null | C1COCCO1 | null | Cl | null | train |
US05391566 | CCCc1cc(CO)cc(Cl)c1O.COC(=O)C(Br)c1ccc2c(c1)OCO2>>CCCc1cc(CO)cc(Cl)c1OC(C(=O)OC)c1ccc2c(c1)OCO2 | null | CC(C)=O | null | O=C([O-])[O-].[K+].[K+] | null | train |
US04921852 | CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C(N)=S)N(C(=O)OCc2ccc([N+](=O)[O-])cc2)C1.NCCN>>CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@H](C2=NCCN2)N(C(=O)OCc2ccc([N+](=O)[O-])cc2)C1 | null | C1CCOC1 | null | null | null | train |
US06586431B1 | COc1cccc(C2(c3ccc(Br)cc3)CNC(=O)CO2)c1>>COc1cccc(C2(c3ccc(Br)cc3)CNCCO2)c1 | null | C1CCOC1 | null | [Na+].[OH-] | [Al+3].[H-].[H-].[H-].[H-].[Li+] | train |
US20100280013A1 | O=C(OO)c1cccc(Cl)c1.c1cnc2c(c1)OCCO2>>[O-][n+]1cccc2c1OCCO2 | null | ClCCl | null | null | null | train |
US04728645 | COC(=O)CCc1c[nH]cn1.ClC(c1ccccc1)(c1ccccc1)c1ccccc1>>COC(=O)CCc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | null | CN(C)C=O | null | CCN(CC)CC | null | train |
US04665189 | OCCCCCCCC=CCCc1ccccc1>>OCCCCCCCCCCCc1ccccc1 | [Pd] | CCO | null | null | null | train |
US20140221311A1 | Nc1cnc(Br)cn1.OB(O)c1ccc(Br)cc1>>Nc1cnc(-c2ccc(Br)cc2)cn1 | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | CCO | CCOC(C)=O | Cc1ccccc1 | O=C([O-])[O-].[K+].[K+] | train |
US20070225494A1 | C1CNCCN1.Cl.Nc1ccccc1Sc1ccccc1C(=O)O>>Cl.c1ccc2c(c1)N=C(N1CCNCC1)c1ccccc1S2 | null | CCO | null | null | null | train |
US06423704B1 | CCOC(=O)c1ccc(CCl)o1.Clc1nc2ccccc2[nH]1>>CCOC(=O)c1ccc(Cn2c(Cl)nc3ccccc32)o1 | null | CCOC(C)=O | null | [H-].[Na+] | null | train |
US04242344 | Clc1cn2c(Cl)cnc2c(N2CCNCC2)n1>>Clc1cnc2c(N3CCNCC3)nccn12 | null | O | null | Cl | null | train |
US20130277609A1 | COB(OC)OC.Oc1ccc(Br)cc1O>>OB(O)c1ccc(O)c(O)c1 | null | C1CCOC1 | null | Cl | [Li]CCCC | train |
US20130012476A1 | Cc1ccc(N)cc1NC(=O)N(C)c1cc(Nc2cccc(N(C)C)c2)ncn1.O=C(Cl)c1cccc(C(F)(F)F)c1>>Cc1ccc(NC(=O)c2cccc(C(F)(F)F)c2)cc1NC(=O)N(C)c1cc(Nc2cccc(N(C)C)c2)ncn1 | null | CN(C)C=O | null | CCN(C(C)C)C(C)C | null | train |
US20020049201A1 | CS(=O)(=O)Cl.Nc1nc2ccccc2[nH]1>>CS(=O)(=O)n1c(N)nc2ccccc21 | null | ClCCl | null | CN(C)C=O | null | train |
US20090143367A1 | Cc1nc(-c2ccccc2Cl)n2c1c(C)nc1cc(OCc3cccc([N+](=O)[O-])c3)ccc12>>Cc1nc(-c2ccccc2Cl)n2c1c(C)nc1cc(OCc3cccc(N)c3)ccc12 | [Ni] | CO | null | NN | O | train |
US20110269765A1 | ClCc1cccc(-c2ncc(Br)cn2)c1.O=c1ccc(Oc2ccccc2)n[nH]1>>O=c1ccc(Oc2ccccc2)nn1Cc1cccc(-c2ncc(Br)cn2)c1 | null | CN(C)C=O | null | O | O=C([O-])[O-].[Cs+].[Cs+] | train |
US05047518 | CI.CO[C@H]1[C@@H]2OC[C@@H](O2)[C@@H](OCc2ccccc2)[C@H]1O>>CO[C@@H]1[C@H](OC)[C@H](OCc2ccccc2)[C@H]2CO[C@@H]1O2 | null | CS(C)=O | null | O | [K+].[OH-] | train |
US04981865 | CN=C=S.COc1ccc2c(c1)c(CNO)c(C)n2C(=O)c1ccc(Cl)cc1>>CNC(=S)N(O)Cc1c(C)n(C(=O)c2ccc(Cl)cc2)c2ccc(OC)cc12 | null | C1COCCO1 | O | null | null | train |
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USPTO_Condition
Overview
This dataset contains reaction data in tabular format, with the following fields:
- source: Source or reference ID of the reaction.
- canonical_rxn: The canonical SMILES representation of the reaction (reactants >> products).
- catalyst1: The catalyst used in the reaction (if available).
- solvent1, solvent2: Solvents used in the reaction (if available).
- reagent1, reagent2: Reagents involved in the reaction (if available).
- dataset: Dataset category or tag.
Example Data
| source | canonical_rxn | catalyst1 | solvent1 | solvent2 | reagent1 | reagent2 | dataset |
|---|---|---|---|---|---|---|---|
| US20070112015A1 | CCOC(=O)CN(CC(C)=O)c1c(C)cc(C)cc1C>>Cc1cc(C)c(N2CC(=O)CC(=O)C2)c(C)c1 | C1CCOC1 | CC(C)(C)[O-].[K+] | val |
Preprocessing
The data was processed following the method described in Parrot - USPTO condition script, ensuring consistent SMILES representations and high-quality condition extraction.
License
The dataset is provided under the MIT License.
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