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

HRID 1249082노트

반응식

HRID 1249082 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-c27088c68fb9428cb9882be74605c639
출처 데이터셋
uspto-grants-1986_12
특허 번호
US04628057

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