Benzoyl chloride → HCID 86736744, compound

HRID 1448111Notes

Reaction equation

HRID 1448111 reaction equation
[C:1]1([CH:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:32]=[CH:31][C:18]4[N:19]([CH2:28][CH2:29][OH:30])[C:20]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[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:39](Cl)(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>N1C=CC=CC=1>[C:33]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:32]=[CH:31][C:18]4[N:19]([CH2:28][CH2:29][O:30][C:39](=[O:46])[C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=5)[C:20]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[N:21][C:17]=4[CH:16]=3)[CH2:10][CH2:9]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 20298772HCID 20298772, compound

Product 1

HCID 86736744HCID 86736744, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred mixture of 5.03 parts of 5-[4-(diphenylmethyl)-1-piperazinylmethyl]-2-phenyl-1H-benzimidazole-1-ethanol and 50 parts of pyridine are added dropwise 3 parts of benzoyl chloride at room temperature. Upon completion, stirring at room temperature is continued for 2 hours. The reaction mixture is evaporated and water is added to the residue. The product is extracted with dichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is crystallized from 20 parts of 2-propanol. The product is filtered off, washed with 2-propanol and with 2,2'-oxybispropane and dried, yielding 4 parts (66.5%) of [2-{5-[4-(diphenylmethyl)-1-piperazinylmethyl]-2-phenyl-1H-benzimidazol-1-yl}ethyl]benzoate; mp. 164.1° C.

Workup

  1. customThe reaction mixture is evaporated
  2. additionwater is added to the residue
  3. extractionThe product is extracted with dichloromethane
  4. washThe extract is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from 20 parts of 2-propanol
  9. filtrationThe product is filtered off
  10. washwashed with 2-propanol and with 2,2'-oxybispropane
  11. customdried

Sources & evidence

ORD record
ord-5e79295a5ae64f4abf84a29d0abe5384
Source dataset
uspto-grants-1979_12
Patent number
US04179505

Reaction notes

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