Chloroacetone → Ethyl 4-methyl-1,3-thiazole-2-carboxylate

HRID 967736

반응식

HRID 967736 반응식
[C:1](OCC)(=[S:5])[C:2]([NH2:4])=O.Cl[CH2:10]C(=O)C.CCCCCC.[C:20]([O:23][CH2:24][CH3:25])(=[O:22])[CH3:21]>C(O)C>[CH3:10][C:2]1[N:4]=[C:21]([C:20]([O:23][CH2:24][CH3:25])=[O:22])[S:5][CH:1]=1

참가 물질

6

반응물 4

HCID 6571ChloroacetoneHCID 8058HexaneHCID 8857Ethyl AcetateHCID 216137632-ethoxy-2-thioxoAcetamide

생성물 1

HCID 567306Ethyl 4-methyl-1,3-thiazole-2-carboxylate수율 22%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Ethyl thiooxamate (3.0 g, 22 mmol) was dissolved in ethanol (30 mL) under argon. Chloroacetone (1.8 mL, 22 mmol) was added and the resultant solution was heated at 80° C. for 16 h. The reaction mixture was concentrated in vacuo, adsorbed onto silica gel, and purified by column chromatography on silica gel eluting with 97:3, then 95:5 hexane:ethyl acetate to afford ethyl 4-methyl-1,3-thiazole-2-carboxylate (850 mg, 22% yield) as an oil. 1H NMR (CDCl3, 300 MHz) 7.20 (s, 1H), 4.48 (q, J=7.1 Hz), 2.56 (s, 3H), 1.47 (s, 3H). MS (EI ionization) 171 (M+).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by column chromatography on silica gel eluting with 97:3

출처 및 근거

ORD 기록
ord-7e12347167a949b9897dc702b39f38aa
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06956049B1

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