Acetyl chloride → HCID 20298800, compound

HRID 1448099Notes

Reaction equation

HRID 1448099 reaction equation
[C:1]1([CH:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:25]=[CH:24][C:18]4[N:19]([CH3:23])[C:20]([NH2:22])=[N:21][C:17]=4[CH:16]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:32](Cl)(=[O:34])[CH3:33].[OH-].[NH4+]>N1C=CC=CC=1>[C:26]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:25]=[CH:24][C:18]4[N:19]([CH3:23])[C:20]([NH:22][C:32](=[O:34])[CH3:33])=[N:21][C:17]=4[CH:16]=3)[CH2:10][CH2:9]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 14923Ammonium HydroxideHCID 20298830HCID 20298830, compound

Product 1

HCID 20298800HCID 20298800, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred mixture of 4.1 parts of 5-[4-(diphenylmethyl)-1-piperazinylmethyl]-1-methyl-1H-benzimidazol-2-amine and 25 parts of pyridine are added dropwise 0.79 parts of acetyl chloride while cooling at 0°-5° C. Upon completion, stirring is continued for one hour at 80° C. The reaction mixture is cooled to room temperature, poured onto ice-water and alkalized with ammonium hydroxide. The product is extracted with methylbenzene. The extract is washed with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 2-propanol. The product is filtered off, washed with 2-propanol and 2,2'-oxybispropane, and dried, yielding 3 parts of N-{5-[4-(diphenylmethyl)-1-piperazinylmethyl]-1-methyl-1H-benzimidazol-2-yl}acetamide; mp. 202.5° C.

Workup

  1. temperaturewhile cooling at 0°-5° C
  2. additionpoured onto ice-water
  3. extractionThe product is extracted with methylbenzene
  4. washThe extract is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by column-chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  10. customThe pure fractions are collected
  11. customthe eluent is evaporated
  12. customThe residue is crystallized from 2-propanol
  13. filtrationThe product is filtered off
  14. washwashed with 2-propanol and 2,2'-oxybispropane
  15. customdried

Sources & evidence

ORD record
ord-c8efe505417a468dbbdcb6937df35a89
Source dataset
uspto-grants-1979_12
Patent number
US04179505

Reaction notes

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