Water → Ethyl 2-amino-4-(trifluoromethyl)-1,3-oxazole-5-carboxylate

HRID 359265Notes

Reaction equation

HRID 359265 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].Cl[CH:6]([C:12]([C:14]([F:17])([F:16])[F:15])=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8].O>CN(C)C=O>[NH2:1][C:2]1[O:3][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:12]([C:14]([F:15])([F:17])[F:16])[N:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1176UreaHCID 2737165Ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoate

Product 1

HCID 21850563Ethyl 2-amino-4-(trifluoromethyl)-1,3-oxazole-5-carboxylateYield 65.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mechanically-stirred mixture of 53.2 g (0.885 mol) of urea and 38.6 g (0.177 mol) of ethyl α-chloro-γ,γ,γ-trifluoroacetoacetate was reacted in 50 ml dry dimethylformamide at 100°-110° C. for 71 hours. The reaction mixture was cooled to ambient temperature and the resulting orange slurry was poured into 500 ml of water and then cooled in an ice bath. Suction filtration of the mixture provided a mustard-colored solid material which when dried under an infrared lamp yielded 26.0 g of material. This solid material was slurried in hot chloroform, then cooled in an ice bath to yield 22.1 g of beige plate-like crystal material (m.p. 193-195° C.). A second crystal crop was obtained after concentration of the slurry residue, recrystallization in hot ether and filtration through glass wool. Total yield was 22.4 g of crystal product (m.p.=193°-195° C.) identified in Table 1.

Workup

  1. temperaturecooled in an ice bath
  2. filtrationSuction filtration of the mixture
  3. customprovided a mustard-colored solid material which when
  4. customdried under an infrared lamp

Sources & evidence

ORD record
ord-8d845874642f4295b08539613f3e527e
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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