Benzaldehyde → (3S)-2-[(4-Chlorobenzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid benzylidenehydrazide

HRID 1249082ノート

反応式

HRID 1249082 の反応式
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][C@@H:3]([C:14]([NH:16][NH2:17])=[O:15])[NH:2]1.[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Cl)=[CH:36][CH:35]=1.[C:42](=[S:44])=[S:43]>CS(C)=O.O>[CH:18](=[N:17][NH:16][C:14]([C@@H:3]1[CH2:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH2:1][N:2]1[C:42]([S:44][CH2:38][C:37]1[CH:40]=[CH:41][C:34]([Cl:33])=[CH:35][CH:36]=1)=[S:43])=[O:15])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

8

反応物 5

HCID 240BenzaldehydeHCID 6348Carbon DisulfideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 8471TriethylamineHCID 7109654(3S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carbohydrazide

生成物 1

HCID 56614200(3S)-2-[(4-Chlorobenzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid benzylidenehydrazide収率 59%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

(3S)-1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acid hydrazide (2.44 g) is dissolved in dimethylsulfoxide (30 ml) and thereto is added benzaldehyde (2 ml). The mixture is stirred at room temperature for 2 hours and thereto are added triethylamine (1.49 ml) and carbon disulfide (0.64 ml). The mixture is stirred at room temperature for one hour and thereto is added dropwise 4-chlorobenzyl chloride (1.7 g). The mixture is stirred at room temperature for 3 hours and thereto is added water. The mixture is extracted with ethyl acetate. The extract is washed with water, dried and distilled to remove the solvent to give the title compound (3.26 g, 59%), as pale yellow powder.

後処理

  1. stirringThe mixture is stirred at room temperature for one hour
  2. stirringThe mixture is stirred at room temperature for 3 hours
  3. extractionThe mixture is extracted with ethyl acetate
  4. washThe extract is washed with water
  5. customdried
  6. distillationdistilled
  7. customto remove the solvent

出典と根拠

ORDレコード
ord-c27088c68fb9428cb9882be74605c639
出典データセット
uspto-grants-1986_12
特許番号
US04628057

反応ノート

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