1,1,1-Trifluoro-2,4-pentanedione → 1-(2-Amino-4-(trifluoromethyl)thiazol-5-yl)ethanone

HRID 1747189Notes

Reaction equation

HRID 1747189 reaction equation
OC1C(OS(C2C=CC(C)=CC=2)(=O)=O)=C(I)C=CC=1.[F:20][C:21]([F:29])([F:28])[C:22](=O)[CH2:23][C:24](=[O:26])[CH3:25].[NH2:30][C:31]([NH2:33])=[S:32]>C(#N)C>[NH2:33][C:31]1[S:32][C:23]([C:24](=[O:26])[CH3:25])=[C:22]([C:21]([F:29])([F:28])[F:20])[N:30]=1

Participants

5

Reactant 3

HCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 2723790ThioureaHCID 21918218Hydroxy tosyloxy iodobenzene

Product 1

HCID 189363001-(2-Amino-4-(trifluoromethyl)thiazol-5-yl)ethanoneYield 89.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Hydroxy(tosyloxy)iodobenzene (3 g, 7.7 mmol) is added to a solution of 1,1,1,-trifluoro pentane-2,4-dione (1 g, 6.4 mmol) in ACN (10 mL). The resulting mixture is heated under reflux for 45 minutes, then cooled down to RT, and thiourea (0.59 g, 7.7 mmol) is added. The mixture is heated under reflux for 4 hours and then left to stand overnight. The reaction mixture is concentrated and the residue is recrystallised in ethylacetate and petroleum ether, affording 1-[2-amino-4-(trifluoromethyl)-1,3-thiazol-5-yl]ethanone (P8) as white solid (1.2 g, 79%).

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureunder reflux for 45 minutes
  3. temperatureThe mixture is heated
  4. temperatureunder reflux for 4 hours
  5. waitleft
  6. concentrationThe reaction mixture is concentrated
  7. customthe residue is recrystallised in ethylacetate

Sources & evidence

ORD record
ord-40da5f8e041a4791b42957e2e3a591ff
Source dataset
uspto-grants-2015_10
Patent number
US09150561B2

Reaction notes

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