Ethyl 2-aminothiazole-4-carboxylate → Ethyl 2-(alpha-bromoacrylamido)thiazole-4-carboxylate

HRID 1290650Notes

Reaction equation

HRID 1290650 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[Br:12][C:13](=[CH2:17])[C:14](O)=[O:15]>O1CCOCC1>[Br:12][C:13](=[CH2:17])[C:14]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1)=[O:15]

Participants

4

Reactant 2

HCID 73216Ethyl 2-aminothiazole-4-carboxylateHCID 826332-Bromoacrylic acid

Product 1

HCID 17876799Ethyl 2-(alpha-bromoacrylamido)thiazole-4-carboxylateYield 85.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution containing 0.688 g of ethyl 2-aminothiazole-4carboxilate (prepared as reported in J.A.C.S. 68,266,1946) and 0.3 g of 2-bromoacrylic acid in 10 ml of dioxane, 0.412 g of N-N'dicyclohexylcarbodiimide were and the mixture was stirred at room temperature overnight. After filtration, the solvent was evaporated in vacuo, the solid residue was dissolved in 50 ml of ethyl acetate, treated with saturated solution of sodium bicarbonate and then with 10% hydrochloric acid. The organic phase was dried over anhydrous sodium sulphate and the solvent evaporated in vacuo. The solid residue was purified by recrystallization from ethanol-water to yield 0.52 g of ethyl 2-(α-bromoacrylamido)thiazole-4-carboxylate.

Workup

  1. filtrationAfter filtration
  2. customthe solvent was evaporated in vacuo
  3. dissolutionthe solid residue was dissolved in 50 ml of ethyl acetate
  4. additiontreated with saturated solution of sodium bicarbonate
  5. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  6. customthe solvent evaporated in vacuo
  7. customThe solid residue was purified by recrystallization from ethanol-water

Sources & evidence

ORD record
ord-16b5e6a84296485abc98721cf20967e5
Source dataset
uspto-grants-1998_05
Patent number
US05753629

Reaction notes

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