Acetyl chloride → N'-acetyl-1-[4-(methylthio)phenyl]-1H-benzimidazole-6-carbohydrazide

HRID 452614Notes

Reaction equation

HRID 452614 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[CH:14]=[C:15]([C:18]([NH:20][NH2:21])=[O:19])[CH:16]=[CH:17][C:12]=3[N:11]=[CH:10]2)=[CH:5][CH:4]=1.[C:22](Cl)(=[O:24])[CH3:23].C(OCC)(=O)C>CN(C)C(=O)C>[C:22]([NH:21][NH:20][C:18]([C:15]1[CH:16]=[CH:17][C:12]2[N:11]=[CH:10][N:9]([C:6]3[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=3)[C:13]=2[CH:14]=1)=[O:19])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 444822941-[4-(methylthio)phenyl]-1H-benzimidazole-6-carbohydrazide

Product 1

HCID 44480701N'-acetyl-1-[4-(methylthio)phenyl]-1H-benzimidazole-6-carbohydrazideYield 100%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 1-[4-(methylthio)phenyl]-1H-benzimidazole-6-carbohydrazide (1.0 g, 3.35 mmol) in N,N-dimethylacetamide (5 mL) was added acetyl chloride (262 μL, 3.69 mmol) at 0° C., and the resulting mixture was stirred at room temperature for 1 hr. Ethyl acetate was added to the reaction mixture, the precipitate was collected by filtration and washed with ethyl acetate to give the title compound (1.14 g, yield 100%) as colorless crystals.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-7c479d5211ee45e49c4c265778dd9e12
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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