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

HRID 560303Notes

Reaction equation

HRID 560303 reaction equation
Br[CH2:2][C:3](=O)[C:4]([F:7])([F:6])[F:5].[NH2:9][C:10]1[S:11][CH:12]=[CH:13][N:14]=1>CC(C)=O>[F:5][C:4]([F:7])([F:6])[C:3]1[N:9]=[C:10]2[N:14]([CH:2]=1)[CH:13]=[CH:12][S:11]2

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 790083-Bromo-1,1,1-trifluoro-2-propanone

Product 1

HCID 110846966-(Trifluoromethyl)imidazo[2,1-b]thiazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Bromo-1,1,1-trifluoroacetone (11.0 mmol) is added to a solution of 2-aminothiazole (10.0 mmol) in acetone (20 mL) and the mixture is stirred at reflux for 20 h. The obtained precipitate is filtered off, treated with hydrobromic acid (2.0 M, 40 mL), stirred at reflux for 1 h and cooled to RT. The mixture is made basic by addition of ammonium hydroxide solution (15%) and the resulting free base is crystallized from EtOH to give the desired product. LC-MS: tR=0.78 min; [M+H]+=192.95.

Workup

  1. temperatureat reflux for 20 h
  2. filtrationThe obtained precipitate is filtered off
  3. additiontreated with hydrobromic acid (2.0 M, 40 mL)
  4. stirringstirred
  5. temperatureat reflux for 1 h
  6. additionThe mixture is made basic by addition of ammonium hydroxide solution (15%)
  7. customthe resulting free base is crystallized from EtOH

Sources & evidence

ORD record
ord-2e777c80f7aa4526b24cc76ede611939
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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