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

HRID 1290650ノート

反応式

HRID 1290650 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-16b5e6a84296485abc98721cf20967e5
出典データセット
uspto-grants-1998_05
特許番号
US05753629

反応ノート

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