Hydrochloric Acid → HCID 14518415, compound

HRID 1723108Notes

Reaction equation

HRID 1723108 reaction equation
[C:1]1([C:7]2[N:11]([CH2:12][CH2:13][CH3:14])[C:10]3[CH:15]=[CH:16][C:17]([CH2:19]O)=[CH:18][C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:21].S(Cl)([Cl:24])=O>ClC(Cl)Cl>[ClH:24].[Cl:21][CH2:19][C:17]1[CH:16]=[CH:15][C:10]2[N:11]([CH2:12][CH2:13][CH3:14])[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:8][C:9]=2[CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 14518413HCID 14518413, compound

Product 1

HCID 14518415HCID 14518415, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(a-5) A solution of 70.5 parts of 2-phenyl-1-propyl-1H-benzimidazole-5-methanol in 300 parts of trichloromethane was saturated with gaseous hydrogen chloride. Then there are added dropwise 55.9 parts of thionyl chloride (exothermic reaction). Upon completion, stirring was continued for 30 minutes at reflux temperature. The reaction mixture was evaporated, the residue was taken up in 90 parts of methylbenzene and the latter was evaporated again. The residue was crystallized from 320 parts of 4-methyl-2-pentanone, yielding 80 parts (96%) of 5-(chloromethyl)-2-phenyl-1-propyl-1H-benzimidazole monohydrochloride; mp. 138.5° C. (int. 61).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. customthe latter was evaporated again
  4. customThe residue was crystallized from 320 parts of 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-9d1d89bdb947450e8337f866057e8b19
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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