Ethyl bromopyruvate → 2-(4-Trifluoromethyl-phenylamino)-thiazole-4-carboxylic acid

HRID 659737Notes

Reaction equation

HRID 659737 reaction equation
C([O:3][C:4](=[O:9])[C:5](=O)[CH2:6]Br)C.[F:10][C:11]([F:23])([F:22])[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH2:21])=[S:20])=[CH:14][CH:13]=1>C(O)C>[F:23][C:11]([F:10])([F:22])[C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19]2[S:20][CH:6]=[C:5]([C:4]([OH:3])=[O:9])[N:21]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 2777727N-[4-(Trifluoromethyl)phenyl]thiourea

Product 1

HCID 27607532-(4-Trifluoromethyl-phenylamino)-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

3-Bromo-2-oxo-propionic acid ethyl ester (0.59 mL) was added to a suspension of (4-trifluoromethyl-phenyl)-thiourea (1 grams), obtained in step (ii) of example-1, in ethanol (20 mL) and refluxed for about 12 hours. The reaction mixture was cooled and the solid obtained was filtered and dissolved in a minimum amount ethanol. 10% sodium hydroxide solution (10 mL) was added and stirred at about 25-35° C. for about 12 hours. The reaction mixture was then diluted with water and acidified with saturated citric acid solution. The solid that precipitated was filtered washed with water and dried to give the product (0.65 grams).

Workup

  1. temperaturerefluxed for about 12 hours
  2. temperatureThe reaction mixture was cooled
  3. customthe solid obtained
  4. filtrationwas filtered
  5. dissolutiondissolved in a minimum amount ethanol
  6. addition10% sodium hydroxide solution (10 mL) was added
  7. additionThe reaction mixture was then diluted with water
  8. customThe solid that precipitated
  9. filtrationwas filtered
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-402430ac4e514c549109c5c833301de1
Source dataset
uspto-grants-2011_12
Patent number
US08080668B2

Reaction notes

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