Isopropanol → 5-[(Ethylsulfamoyl)acetyl]-1,4-dihydro-2-methyl-4-(3-nitrophenyl)nicotinic acid methyl ester

HRID 1252248Notes

Reaction equation

HRID 1252248 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].[CH2:19]([NH:21][S:22]([CH2:25][C:26](=[O:30])[CH:27]=[CH:28][NH2:29])(=[O:24])=[O:23])[CH3:20].[C:31](#N)[CH3:32].[CH:34]([OH:37])(C)C>CN(C)C=O>[CH3:34][O:37][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:27]([C:26](=[O:30])[CH2:25][S:22](=[O:24])(=[O:23])[NH:21][CH2:19][CH3:20])=[CH:28][NH:29][C:31]=1[CH3:32]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 6342AcetonitrileHCID 534430103-Nitrobenzylideneacetoacetic acid methyl esterHCID 73663801N-ethyl-4-amino-2-oxo-3-butenesulfonamide

Product 1

HCID 704165005-[(Ethylsulfamoyl)acetyl]-1,4-dihydro-2-methyl-4-(3-nitrophenyl)nicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After boiling 2.5 g of 3-nitrobenzylideneacetoacetic acid methyl ester and 1.92 g of N-ethyl-4-amino-2-oxo-3-butenesulfonamide in a mixture of 10 ml of isopropanol and 5 ml of dimethylformamide for 6 hours there were obtained 2.2 g of 5-[(ethylsulfamoyl)acetyl]-1,4-dihydro-2-methyl-4-(3-nitrophenyl)nicotinic acid methyl ester of melting point 185°-187° (yellow crystalline powder from acetonitrile).

Sources & evidence

ORD record
ord-b712a5aa9ead467485ffa3be7f6cfa1c
Source dataset
uspto-grants-1988_05
Patent number
US04742069

Reaction notes

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