Isopropanol → 5-(Isopropylsulfamoyl)-1,4-dihydro-2.6-dimethyl-4-(3-nitrophenyl)nicotinic acid 2-propoxyethyl ester

HRID 982288Notes

Reaction equation

C([C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1)=[CH:5][S:6]([NH:9][CH:10]([CH3:12])[CH3:11])(=[O:8])=[O:7])(=O)C.[CH2:22]([O:25][CH2:26][CH2:27][O:28][C:29](=[O:34])/[CH:30]=[C:31](\[NH2:33])/[CH3:32])[CH2:23][CH3:24].[CH:35](O)(C)[CH3:36]>>[CH2:22]([O:25][CH2:26][CH2:27][O:28][C:29](=[O:34])[C:30]1[CH:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[C:5]([S:6](=[O:7])(=[O:8])[NH:9][CH:10]([CH3:11])[CH3:12])=[C:35]([CH3:36])[NH:33][C:31]=1[CH3:32])[CH2:23][CH3:24]

Participants

Reactant 3

HCID 3776Isopropanol

HCID 125291902-(n-Propoxy)ethyl 3-aminocrotonate

HCID 54206999alpha-acetyl-N-isopropyl-3-nitrostyrenesulfonamide

Product 1

HCID 679461735-(Isopropylsulfamoyl)-1,4-dihydro-2.6-dimethyl-4-(3-nitrophenyl)nicotinic acid 2-propoxyethyl esterYield 21%

Procedure

A solution of 3.12 g (0.01 mol) of α-acetyl-N-isopropyl-3-nitrostyrenesulfonamide in 30 ml of isopropanol is treated with 1.87 g (0.01 mol) of 3-aminocrotonic acid 2-propoxyethyl ester and 1.16 g (0.005 mol) of DL-camphor-10-sulfonic acid in accordance with the procedure described in Example 1. After chromatography on silica gel with methylene chloride/ethyl acetate (4:1) as the elution agent the crude product is recrystallized from isopropanol. There is obtained 1.0 g (21%) of 5-(isopropylsulfamoyl)-1,4-dihydro-2.6-dimethyl-4-(3 -nitrophenyl)nicotinic acid 2-propoxyethyl ester, m.p. 155°-158°, as a colorless crystalline powder.

Workup

customAfter chromatography on silica gel with methylene chloride/ethyl acetate (4:1) as the elution agent the crude product is recrystallized from isopropanol

Sources & evidence

ORD record: ord-810bae2098ef4701bf0930594de35382
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04994612

Reaction notes

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