Ethyl thiooxamate → Ethyl 4-[3-(trifluoromethyl)phenyl]-1,3-thiazole-2-carboxylate

HRID 1257462Notes

Reaction equation

HRID 1257462 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)=O.[NH2:15][C:16](=[S:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>>[F:12][C:11]([F:14])([F:13])[C:7]1[CH:6]=[C:5]([C:3]2[N:15]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[S:22][CH:2]=2)[CH:10]=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 2733398Ethyl thiooxamateHCID 27783862-Bromo-1-[3-(trifluoromethyl)phenyl]ethan-1-one

Product 1

HCID 10424923Ethyl 4-[3-(trifluoromethyl)phenyl]-1,3-thiazole-2-carboxylateYield 49%

Conditions

Temperature
80 °C

Procedure

To 2-bromo-1-[3-(trifluoromethyl)phenyl]ethanone (14 g, 41 mmol) was added ethyl amino(thioxo)acetate (5.0 g, 38 mmol), and the mixture was stirred at 80° C. for 3 hr. The solvent was evaporated under reduced pressure, and the obtained crude product was purified by recrystallization (ethyl acetate) to give the title compound (5.6 g, 49%) as colorless crystals.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe obtained crude product
  3. customwas purified by recrystallization (ethyl acetate)

Sources & evidence

ORD record
ord-24e1736126a041aea6279d4158432356
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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