Diethyl 2-(chloromethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate → 2-(Phenylthio)methyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

HRID 1493306

반응식

HRID 1493306 반응식
Cl[CH2:2][C:3]1[NH:4][C:5]([CH3:28])=[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]([O-])=O.[Na+].[CH3:38]CO.COCCOC>C(O)C>[C:30]1([S:34][CH2:2][C:3]2[NH:4][C:5]([CH3:28])=[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:7]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=3)[C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:38]=[CH:29][CH:33]=[CH:32][CH:31]=1

참가 물질

5

반응물 3

HCID 3064723Diethyl 2-(chloromethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateHCID 20074477Dimethoxyethane ethanolHCID 23672340Sodium 2-thenoate

생성물 1

HCID 198311872-(Phenylthio)methyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 2-chloromethyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine (5.6 g) in EtOH/DME (5/1; 20 ml) is added dropwise at +10° C. to a stirred solution of sodium thiophenate (1.8 g) in ethanol (10 ml), under N2 atmosphere. After two hours at room temperature the reaction mixture is evaporated under vacuum and the residue is partitioned between Et2O (100 ml) and water (50 ml). The organic phase is washed with a satured solution of sodium bicarbonate (2×20 ml) and water (3×20 ml), dried (Na2SO4) and evaporated to dryness. The residue is recrystallized from isopropylether to give 5.7 g of 2-(phenylthio)methyl-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine, m.p. 92°-94° C.

후처리

  1. customAfter two hours at room temperature the reaction mixture is evaporated under vacuum
  2. customthe residue is partitioned between Et2O (100 ml) and water (50 ml)
  3. washThe organic phase is washed with a satured solution of sodium bicarbonate (2×20 ml) and water (3×20 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. customThe residue is recrystallized from isopropylether

출처 및 근거

ORD 기록
ord-49b6f32372b04ae5aff401bf11842f9c
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05021436

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