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

HRID 1925215Notes

Reaction equation

HRID 1925215 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-one2×

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 (23.7 g, 0.23 mol) and 2-bromo-4′-fluoroacetophenone (alternatively named: 2-bromo-1-(4-fluorophenyl)-ethanone) (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 (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-5e81ded710324c1ead31e5ea481fc1c1
Source dataset
uspto-grants-2012_05
Patent number
US08178672B2

Reaction notes

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