Thionyl Chloride → 1-Phenacyl-2-(2-chloroethylamino)benzimidazole hydrochloride

HRID 54691Notes

Reaction equation

HRID 54691 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][NH:8][C:9]1[N:13]([CH2:14][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])[C:12]2[CH:23]=[CH:24][CH:25]=[CH:26][C:11]=2[N:10]=1>C(Cl)(Cl)Cl>[ClH:3].[CH2:14]([N:13]1[C:12]2[CH:23]=[CH:24][CH:25]=[CH:26][C:11]=2[N:10]=[C:9]1[NH:8][CH2:7][CH2:6][Cl:3])[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 28501002-{2-[(2-hydroxyethyl)amino]-1H-benzimidazol-1-yl}-1-phenylethanone

Product 1

HCID 190408301-Phenacyl-2-(2-chloroethylamino)benzimidazole hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Add 0.7 ml (10 mmol) of freshly distilled thionyl chloride, with stirring, to a suspension of 1.5 g (5 mmol) of the base obtained above in 25 ml of anhydrous chloroform. Heat the resulting solution at reflux for 1 hour. After cooling, the 1-phenacyl-2-(2-chloroethylamino)benzimidazole hydrochloride precipitate is isolated by filtration, washed with petroleum ether and recrystallised from a mixture of ethanol/ether.

Workup

  1. temperatureHeat the resulting solution
  2. temperatureat reflux for 1 hour
  3. temperatureAfter cooling

Sources & evidence

ORD record
ord-7555846cb41b4fb190495861083de511
Source dataset
uspto-grants-1997_04
Patent number
US05623073

Reaction notes

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