2-Aminothiazole → 6-(4-Fluorophenyl)imidazo[2,1-b][1,3]thiazole

HRID 600256Notes

Reaction equation

HRID 600256 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.Br[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=O.[OH-].[NH4+]>C(O)C>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:1]=[C:2]3[N:6]([CH:8]=2)[CH:5]=[CH:4][S:3]3)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 14923Ammonium HydroxideHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-one

Product 1

HCID 8681986-(4-Fluorophenyl)imidazo[2,1-b][1,3]thiazoleYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-aminothiazole (H) (23.7 g, 0.23 mol) and 2-bromo-1-(4-fluorophenyl)-ethanone (I) (50 g, 0.23 mol) is added absolute ethanol (600 mL). The reaction is allowed to reflux with vigorous stirring for 16 hours. The reaction mixture is reduced to half its original volume in vacuo. The remaining liquid is poured onto ice and the solution made basic by the addition of ammonium hydroxide solution (30%). The resulting fine solid is filtered and washed with water. The dark yellow solid so obtained is dried in a vacuum oven at 50° C. to provide 6-(4-fluorophenyl)-imidazo[2,1-b]thiazole (J) (43.0 g, 86%).

Workup

  1. temperatureto reflux
  2. additionThe remaining liquid is poured onto ice
  3. filtrationThe resulting fine solid is filtered
  4. washwashed with water
  5. customThe dark yellow solid so obtained
  6. customis dried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-9da37d17db9847e7a8317c54098562e8
Source dataset
uspto-grants-2011_03
Patent number
US07902192B2

Reaction notes

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