Acetic Anhydride → HCID 131711667, compound

HRID 1448106Notes

Reaction equation

HRID 1448106 reaction equation
[C:1]1([CH:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:26]=[CH:25][C:18]4[N:19]([CH3:24])[C:20]([CH2:22][OH:23])=[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:33](OC(=O)C)(=[O:35])[CH3:34]>CC1C=CC=CC=1>[C:27]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:26]=[CH:25][C:18]4[N:19]([CH3:24])[C:20]([CH2:22][O:23][C:33](=[O:35])[CH3:34])=[N:21][C:17]=4[CH:16]=3)[CH2:10][CH2:9]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 19890747HCID 19890747, compound

Product 1

HCID 131711667HCID 131711667, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1.9 parts of 5-[4-(diphenylmethyl)-1-piperazinylmethyl]-1-methyl-1H-benzimidazole-2-methanol, 1.55 parts of acetic acid anhydride and 45 parts of methylbenzene is stirred and refluxed for 2 hours. The reaction mixture is cooled, washed with a diluted ammonium hydroxide solution and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is crystallized from a mixture of methylbenzene and 2,2'-oxybispropane (20:20 by volume). The product is filtered off and dried, yielding 1.5 parts (74.4%) of {5-[4-(diphenylmethyl)-1-piperazinylmethyl]-1-methyl-1H-benzimidazol-2-ylmethyl}acetate; mp. 201.1° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe reaction mixture is cooled
  3. washwashed with a diluted ammonium hydroxide solution
  4. customthe layers are separated
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from a mixture of methylbenzene and 2,2'-oxybispropane (20:20 by volume)
  9. filtrationThe product is filtered off
  10. customdried

Sources & evidence

ORD record
ord-7b537ddc0ecf45fcae9726bd775bf79c
Source dataset
uspto-grants-1979_12
Patent number
US04179505

Reaction notes

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