Hydrochloric Acid → 1-(METHYLSULFONYLOXY)-6-CHLORO-2-(TRIFLUOROMETHYL)-1H-IMIDAZO(4,5-b)PYRIDINE

HRID 2082648Notes

Reaction equation

[OH:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]=[C:3]1[C:12]([F:15])([F:14])[F:13].[CH3:16][S:17](Cl)(=[O:19])=[O:18].Cl>N1C=CC=CC=1>[CH3:16][S:17]([O:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]=[C:3]1[C:12]([F:15])([F:14])[F:13])(=[O:19])=[O:18]

Participants

Conditions

Temperature: 5 °C

Procedure

1-Hydroxy-6-chloro-2-(trifluoromethyl)-1H-imidazo-(4,5-b)pyridine (5 grams) in 15 milliliters of pyridine was cooled to 5° C. with stirring and methylsulfonyl chloride (5 milliliters) was added in 1-milliliter portions, maintaining the temperature at about 5° C. After the addition was completed, the reaction mixture was stirred for two hours at 5°-10° C., then poured into 30 grams of ice and 20 milliliters of concentrated hydrochloric acid. The desired 1-(methylsulfonyloxy)-6-chloro-2-(trifluoromethyl)- 1H-imidazo(4,5-b)pyridine product precipitated and was separated by filtration and washed with water. The washed product was taken up in diethyl ether with a trace of acetone, dried over magnesium sulfate and the solvent evaporated under vacuum. The product so obtained melted at 136.7° C.

Workup

additionAfter the addition
stirringthe reaction mixture was stirred for two hours at 5°-10° C.
customThe desired 1-(methylsulfonyloxy)-6-chloro-2-(trifluoromethyl)- 1H-imidazo(4,5-b)pyridine product precipitated
customwas separated by filtration
washwashed with water
dry with materialdried over magnesium sulfate
customthe solvent evaporated under vacuum

Sources & evidence

ORD record: ord-473b290b4d4945c693745cb8e6d3865b
Source dataset: uspto-grants-1978_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04082534

Reaction notes

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