Thionyl Chloride → 2-(Chloromethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine hydrochloride

HRID 1444739Notes

Reaction equation

O[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:18])=O>C(Cl)Cl.C1(C)C=CC=CC=1>[ClH:18].[Cl:18][CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][N:4]=1

Participants

Conditions

Temperature: 2.5 °C

Procedure

160 ml of toluene were added to 14.9 g (0.067 mole) of 2-hydroxymethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine in methylene chloride followed by distillation of methylene chloride. The solution was purified with 2.7 g of activated charcoal, filtered and washed with 36 ml of toluene. To this solution 5.4 ml (0.075 mole) of thionyl chloride in 27 ml of toluene were added dropwise and maintained for 3 hours. The gas was removed under vacuum at room temperature, then the resulting mixture was cooled to a temperature of from 0 to 5° C. and stirred for one hour. The product was filtered, washed with 3 ml of toluene and dried in a vacuum dryer at 35-40° C. The yield was 15.65 g (84%).

Workup

distillationfollowed by distillation of methylene chloride
customThe solution was purified with 2.7 g of activated charcoal
filtrationfiltered
washwashed with 36 ml of toluene
temperaturemaintained for 3 hours
customThe gas was removed under vacuum at room temperature
filtrationThe product was filtered
washwashed with 3 ml of toluene
customdried in a vacuum dryer at 35-40° C

Sources & evidence

ORD record: ord-10d5eb53e54a42e284e8f4386aecd2b0
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662968B2

Reaction notes

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