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

HRID 975043Notes

Reaction equation

HRID 975043 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>[C:24]([C:23]1[S:32][C:31]([NH2:33])=[N:30][C:22]=1[C:21]([F:29])([F:28])[F:20])(=[O:26])[CH3:25]

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)ethanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Hydroxy(tosyloxy)iodobenzene (78.5 g) was added to a solution of 1,1,1-trifluoropentane-2,4-dione in acetonitrile (500 ml). The mixture was heated under reflux for 45 minutes, then cooled, and thiourea (15.2 g) was added. The mixture was heated under reflux for 4 hours and then left to stand overnight. Evaporation and crystallisation of the residue from dichloromethane gave the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 45 minutes
  3. temperaturecooled
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for 4 hours
  6. waitleft
  7. customEvaporation and crystallisation of the residue from dichloromethane

Sources & evidence

ORD record
ord-ccad7cee74544156972c975bcf2df11d
Source dataset
uspto-grants-1997_03
Patent number
US05607956

Reaction notes

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