Hydrochloric Acid → HCID 20298748, compound

HRID 1448109Notes

Reaction equation

HRID 1448109 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]O)[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.Cl.S(Cl)([Cl:42])=O>ClC(Cl)Cl>[Cl:42][CH2:29][CH2:28][N:19]1[C:18]2[CH:31]=[CH:32][C:15]([CH2:14][N:11]3[CH2:10][CH2:9][N:8]([CH:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH2:13][CH2:12]3)=[CH:16][C:17]=2[N:21]=[C:20]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 20298772HCID 20298772, compound

Product 1

HCID 20298748HCID 20298748, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred mixture of 5.03 parts of 5-[4-(diphenylmethyl)-1-piperazinylmethyl]-2-phenyl-1H-benzimidazole-1-ethanol and 75 parts of trichloromethane is acidified by the introduction of gaseous hydrogen chloride. Then there are added dropwise 2.4 parts of thionyl chloride at room temperature. Upon completion, stirring is continued for 20 minutes at reflux. The reaction mixture is evaporated. 100 Parts of water are added to the residue and the whole is alkalized with sodium hydrogen carbonate. The product is extracted with dichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is purified by columnchromatography 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 methylbenzene. The product is filtered off and dried, yielding 3.1 parts of 1-(2-chloroethyl)-5-[4-(diphenylmethyl)-1-piperazinylmethyl]-2-phenyl-1H-benzimidazole; mp. 173.8°-179.6° C.

Workup

  1. temperatureat reflux
  2. customThe reaction mixture is evaporated
  3. addition100 Parts of water are added to the residue
  4. extractionThe product is extracted with dichloromethane
  5. washThe extract is washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by columnchromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated
  13. customThe residue is crystallized from methylbenzene
  14. filtrationThe product is filtered off
  15. customdried

Sources & evidence

ORD record
ord-9dd7d61f83864a48ba5216ec323f323c
Source dataset
uspto-grants-1979_12
Patent number
US04179505

Reaction notes

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