Thioacetamide → HCID 19431928, compound

HRID 1077565Notes

Reaction equation

HRID 1077565 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[N:18]([S:22]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[C:17]1[CH:16]=[N:15][C:14]([C:32](=O)[CH2:33]Br)=[C:13]([CH2:36][O:37][CH3:38])[C:12]2=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:39]([NH2:42])(=[S:41])[CH3:40]>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[N:18]([S:22]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)(=[O:23])=[O:24])[C:17]1[CH:16]=[N:15][C:14]([C:32]3[N:42]=[C:39]([CH3:40])[S:41][CH:33]=3)=[C:13]([CH2:36][O:37][CH3:38])[C:12]2=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 86749704HCID 86749704, compound

Product 1

HCID 19431928HCID 19431928, compoundYield 51,105.602%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.530 g of 6-benzyloxy-3-bromoacetyl-4-methoxymethyl-9-tosyl-β-carboline is refluxed for 3 hours in 50 ml of ethanol with 0.07 g of thioacetamide. After concentration by evaporation the residue is chromatographed on silica gel with cyclohexane and ethyl acetate=1+1 as eluant. 0,260 g of 6-benzyloxy-4-methoxymethyl-3-(2-methyl-4-thiazolyl)-9-tosyl-β-carboline of a melting point 181°-182° C. is obtained.

Workup

  1. concentrationAfter concentration
  2. customby evaporation the residue
  3. customis chromatographed on silica gel with cyclohexane and ethyl acetate=1+1 as eluant

Sources & evidence

ORD record
ord-38719a3c137c4411963f4bfafaf4028d
Source dataset
uspto-grants-1996_08
Patent number
US05543519

Reaction notes

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