Clofibric Acid → 2-(4-Chlorophenoxy)-2-methylpropanoyl chloride

HRID 323936

Reaction equation

HRID 323936 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8](O)=[O:9])=[CH:4][CH:3]=1.S(Cl)([Cl:17])=O>>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8]([Cl:17])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2797Clofibric AcidHCID 24386Thionyl Chloride

Product 1

HCID 27813122-(4-Chlorophenoxy)-2-methylpropanoyl chloride

Procedure

A mixture of 2-(4-chlorophenoxy)-2-methylpropionic acid (15.0 g) and thionyl chloride (70 ml) was boiled under reflux for 1 hour. The thionyl chloride was distilled off and the residue distilled under vacuum to give 2- (4-chlorophenoxy) -2-methylpropionyl chloride, b.p. 84-87° C. at 0.07 mbar. A solution of this chloride (14.17 g) in dichloromethane (50 ml) was added dropwise to a mixture of 1-(3-aminopropyl)imidazole (7.63 g), triethylamine (6.78 g) and dichloromethane (100 ml) at below 0° C. with stirring. After the addition, the mixture was allowed to warm up to ambient temperature and stirred at this temperature for 2 hours. Saturated aqueous sodium bicarbonate solution (100 ml) was added and the mixture stirred for 1 hour. The mixture was separated and the aqueous layer was washed with dichloromethane. The combined organic layers were dried and evaporated to give a solid which was recrystallised from ethyl acetate to give 2-(4-chlorophenoxy)-N-[3-(imidazol-1-yl)propyl ]-2-methylpropionamide, m.p. 83-84° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. distillationThe thionyl chloride was distilled off
  3. distillationthe residue distilled under vacuum

Sources & evidence

ORD record
ord-17c18c233dd84fb5a1a63125522233ec
Source dataset
uspto-grants-2001_04
Patent number
US06215001B1

Linked notes

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