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

HRID 1249082Notes

Reaction equation

HRID 1249082 reaction equation
[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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

(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.

Workup

  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

Sources & evidence

ORD record
ord-c27088c68fb9428cb9882be74605c639
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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