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

反応式

HRID 1493306 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-49b6f32372b04ae5aff401bf11842f9c
出典データセット
uspto-grants-1991_06
特許番号
US05021436

関連ノート

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