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

HRID 2405118Notes

Reaction equation

HRID 2405118 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-d660b9f9010c40d99c372ddb6a5b0319
Source dataset
uspto-grants-2014_08
Patent number
US08802861B2

Reaction notes

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