Ethyl bromopyruvate → Ethyl 2-(phenylamino)-4-thiazolecarboxylate

HRID 2107259Notes

Reaction equation

HRID 2107259 reaction equation
[C:1]1([NH:7][C:8]([NH2:10])=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:12][C:13](=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)C>[NH:7]([C:8]1[S:9][CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:10]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 676454Phenylthiourea

Product 1

HCID 15053537Ethyl 2-(phenylamino)-4-thiazolecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprising 8.6 g of phenylthiourea, 10 g of ethyl bromopyruvate and 100 ml of ethanol was heated under reflux for 3 hours, and the reaction mixture was then concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the residue, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crystals which formed were collected by filtration. washed with benzene, and then recrystallized from ethanol, giving the desired compound as pale yellow prismatic crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. concentrationthe reaction mixture was then concentrated under reduced pressure
  4. additionA saturated aqueous sodium hydrogen carbonate solution was added to the residue
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe crystals which formed
  9. filtrationwere collected by filtration
  10. washwashed with benzene
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ea8ac3e93ee34a57b5ef4f1bed6fe4e6
Source dataset
uspto-grants-1990_06
Patent number
US04933355

Reaction notes

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