Ethyl bromopyruvate → Ethyl 2-(4-(trifluoromethyl)phenyl)thiazole-4-carboxylate

HRID 1748606Notes

Reaction equation

HRID 1748606 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[S:8])=[CH:5][CH:4]=1.Br[CH2:15][C:16](=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(O)C>[CH2:20]([O:19][C:17]([C:16]1[N:9]=[C:7]([C:6]2[CH:10]=[CH:11][C:3]([C:2]([F:1])([F:12])[F:13])=[CH:4][CH:5]=2)[S:8][CH:15]=1)=[O:18])[CH3:21]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 27348234-(Trifluoromethyl)thiobenzamide

Product 1

HCID 2737237Ethyl 2-(4-(trifluoromethyl)phenyl)thiazole-4-carboxylateYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(trifluoromethyl)thiobenzamide (5.24 g) in ethanol (50 ml) was added 90% ethyl bromopyruvate (5.53 g), and stirred at 80° C. for 2.5 hours. After completion of the reaction, the solvent was evaporated, and water was added thereto. The insoluble matter was collected by filtration, and then dried to give the titled compound (7.56 g) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. additionwater was added
  4. filtrationThe insoluble matter was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-9b1de884ed43433899f771375c38ed14
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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