Isopropanol → 1,4-Dihydro-2,6-dimethyl-5-[(dimethylsulfamoyl)acetyl]-4-(3-nitrophenyl)nicotinic acid methyl ester

HRID 1252249Notes

Reaction equation

HRID 1252249 reaction equation
COC(=O)C[C:5]([CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)=[O:6].[NH2:19][C:20]([CH3:31])=[CH:21][C:22](=[O:30])[CH2:23][S:24]([N:27]([CH3:29])[CH3:28])(=[O:26])=[O:25].[CH:32](O)(C)[CH3:33].CN(C)[CH:38]=[O:39]>C(O)C>[CH3:38][O:39][C:5](=[O:6])[C:7]1[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:21]([C:22](=[O:30])[CH2:23][S:24](=[O:25])(=[O:26])[N:27]([CH3:29])[CH3:28])=[C:20]([CH3:31])[NH:19][C:32]=1[CH3:33]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 6228DimethylformamideHCID 534430103-Nitrobenzylideneacetoacetic acid methyl esterHCID 736638054-amino-N,N-dimethyl-2-oxo-3-pentenesulfonamide

Product 1

HCID 700466411,4-Dihydro-2,6-dimethyl-5-[(dimethylsulfamoyl)acetyl]-4-(3-nitrophenyl)nicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After boiling 2.5 g of 3-nitrobenzylidene-acetoacetic acid methyl ester and 2.06 g of 4-amino-N,N-dimethyl-2-oxo-3-pentenesulfonamide is a mixture of 10 ml of isopropanol and 5 ml of dimethylformamide for 6 hours there were obtained 2.3 g of 1,4-dihydro-2,6-dimethyl-5-[(dimethylsulfamoyl)acetyl]-4-(3-nitrophenyl)nicotinic acid methyl ester of melting point 154°-157° (yellow crystalline powder from ethanol).

Sources & evidence

ORD record
ord-5988f0e3c6094f8a9e3c90e6860c6df5
Source dataset
uspto-grants-1988_05
Patent number
US04742069

Reaction notes

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