Carbon Disulfide → HCID 178492021, compound

HRID 452608Notes

Reaction equation

HRID 452608 reaction equation
[CH3:1][O: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.[OH-].[K+].[C:24](=S)=[S:25]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]3[CH:14]=[C:15]([C:18]4[O:19][C:24]([SH:25])=[N:21][N:20]=4)[CH:16]=[CH:17][C:12]=3[N:11]=[CH:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 686633771-(4-methoxyphenyl)-1H-benzimidazole-6-carbohydrazide

Product 1

HCID 178492021HCID 178492021, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(4-methoxyphenyl)-1H-benzimidazole-6-carbohydrazide (1.09 g, 3.86 mmol), potassium hydroxide (0.32 g, 5.79 mmol), carbon disulfide (2.31 mL, 38.6 mmol) and ethanol (20 mL) was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, N,N-dimethylformamide (15 ml) was added to the residue, and the resulting mixture was stirred at 100° C. overnight. The reaction mixture was acidified with 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was washed with water to give the title compound (0.66 g, yield 53%) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, N,N-dimethylformamide (15 ml)
  2. additionwas added to the residue
  3. stirringthe resulting mixture was stirred at 100° C. overnight
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe residue was washed with water

Sources & evidence

ORD record
ord-ce8b256dc9ee4ea083bc347526dd4faf
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

Loading…