2-Aminothiazole → 6-(2,4-Difluorophenyl)imidazo[2,1-b]thiazole

HRID 1930044Notes

Reaction equation

HRID 1930044 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[F:12])=O.[S:13]1[CH:17]=[CH:16][N:15]=[C:14]1[NH2:18]>CCO>[F:12][C:6]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=1[C:3]1[N:18]=[C:14]2[N:15]([CH:2]=1)[CH:16]=[CH:17][S:13]2

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 27741852-Bromo-2',4'-difluoroacetophenone

Product 1

HCID 594578316-(2,4-Difluorophenyl)imidazo[2,1-b]thiazoleYield 77.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

The 2-bromo-1-(2,4-difluorophenyl)ethanone (7.50 g, 31.9 mmol) and thiazol-2-amine (3.20 g, 31.9 mmol) were added to EtOH (85 mL) and then heated to about 85° C. in an oil bath for about 16 h. The mixture was cooled in ice water, filtered, and washed with EtOH. Drying under vacuum at about 60° C. provided the title compound (5.84 g, 77%): LC/MS (Table 1, Method a) Rt=2.68 min; MS m/z: 237.3 (M+H)+.

Workup

  1. filtrationfiltered
  2. washwashed with EtOH
  3. customDrying under vacuum at about 60° C.

Sources & evidence

ORD record
ord-546ea37a0bbd495890f1aa2c0d24acbe
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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