Sodium Carbonate → 4-Thiazolecarboxylic acid, 5-phenyl-2-(trifluoromethyl)-, ethyl ester

HRID 383927Notes

Reaction equation

HRID 383927 reaction equation
Cl[CH:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[F:16][C:17]([F:22])([F:21])[C:18]([NH2:20])=[S:19].C([O-])([O-])=O.[Na+].[Na+]>CC#N>[C:10]1([C:2]2[S:19][C:18]([C:17]([F:22])([F:21])[F:16])=[N:20][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 4425751TrifluoroethanethioamideHCID 13833360Ethyl 3-chloro-2-oxo-3-phenylpropanoate

Product 1

HCID 592913484-Thiazolecarboxylic acid, 5-phenyl-2-(trifluoromethyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl 3-chloro-2-oxo-3-phenylpropanoate and trifluorothioacetamide in MeCN was heated under reflux. To the reaction mixture was added an aqueous Na2CO3 solution, followed by extraction with EtOAc. The organic layer was washed with water and brine in this order, dried, and then concentrated under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane: EtOAc) to obtain ethyl 5-phenyl-2-(trifluoromethyl)-1,3-thiazole-4-carboxylate as a white solid.

Workup

  1. temperatureunder reflux
  2. extractionfollowed by extraction with EtOAc
  3. washThe organic layer was washed with water and brine in this order
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane: EtOAc)

Sources & evidence

ORD record
ord-4aba71c0bc784a9fb07d98cc7ee5226f
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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