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

HRID 2801
Notes
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Reaction equation

HRID 2801 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-ea8d9c1fc5de4b569364ab4d8c41abcc
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05731335

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes