Hydrogen Sulfide → 2-Mercaptomethyl-3,5-dicarboetoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

HRID 358985

반응식

HRID 358985 반응식
[O-]CC.[Na+].S.Cl[CH2:7][C:8]1[NH:9][C:10]([CH3:33])=[C:11]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].O[S:35](O)(=O)=O>COCCOC.O>[SH:35][CH2:7][C:8]1[NH:9][C:10]([CH3:33])=[C:11]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

참가 물질

7

반응물 4

HCID 402Hydrogen SulfideHCID 1118Sulfuric AcidHCID 2723922Sodium ethoxideHCID 3064723Diethyl 2-(chloromethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

생성물 1

HCID 116758332-Mercaptomethyl-3,5-dicarboetoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
-15 °C

실험 절차

A stirred ethanolic solution (200 ml) of an alkaline alkoxide, for example sodium ethoxide (20 g), is saturated, at +10° C., with dry hydrogen sulfide, cooled to -15° C., and added with a solution of 2-chloromethyl-3,5-dicarboethoxy-4-(m-nitrophenyl) -6-methyl-1,4-dihydropyridine (25 g) in DME (70 ml). After one hour, the reaction mixture is warmed to 0° C., acidified with H2SO4 (10% water solution; 100 ml) and diluted with water (1400 ml). The precipitate is filtered off, dried in vacuum, and recrystallized from Et2O to give 23 g of 2-mercaptomethyl-3,5-dicarboethoxy-4-(m-nitrophenyl) -6-methyl-1,4-dihydropyridine, m.p. 145°-147° C.

후처리

  1. temperaturethe reaction mixture is warmed to 0° C.
  2. filtrationThe precipitate is filtered off
  3. customdried in vacuum
  4. customrecrystallized from Et2O

출처 및 근거

ORD 기록
ord-3c448e32a23e4d4da5273b36e9f225c6
출처 데이터셋
uspto-grants-1991_03
특허 번호
US04999362

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