Water → Imidazo (2,1-b)-1,3,4-thiadiazole, 2-(methoxymethyl)-6-(trifluoromethyl)-

HRID 1851708Notes

Reaction equation

Br[CH2:2][C:3]([C:5]([F:8])([F:7])[F:6])=O.[CH3:9][O:10][CH2:11][C:12]1[S:16][C:15]([NH2:17])=[N:14][N:13]=1.O>COCCOC>[CH3:9][O:10][CH2:11][C:12]1[S:16][C:15]2=[N:17][C:3]([C:5]([F:8])([F:7])[F:6])=[CH:2][N:14]2[N:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Bromotrifluoroacetone (478 g, 2.5 mol, 1.05 eq) is added on a suspension of 5-(methoxymethyl)-1,3,4-thiadiazol-2-amine a1 (346 g, 2.4 mol, 1 eq) in 1,2-dimethoxyethane (6 l) at 20° C. The reaction mixture is heated to 80° C. until maximum conversion (<24 h). Water (4 l) is added to the reaction mixture at 32° C. and the expected compound crystallized out of the reaction mixture. The crystalline suspension is cooled to 10° C. to complete the crystallization process, filtered and the crystalline precipitate is washed with water (1.5 l) to afford 266 g of pure 2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole a2.

Workup

customthe expected compound crystallized out of the reaction mixture
temperatureThe crystalline suspension is cooled to 10° C.
filtrationfiltered
washthe crystalline precipitate is washed with water (1.5 l)

Sources & evidence

ORD record: ord-81d231f8616b473cac31b28bb33a7588
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957218B2

Reaction notes

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