2-Bromo-1-(3,4-dimethoxyphenyl)ethan-1-one → 4-(3,4-Dimethoxyphenyl)-2-methyl-1,3-thiazole

HRID 10689

반응식

HRID 10689 반응식
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)=O.[C:15]([NH2:18])(=[S:17])[CH3:16]>C(O)C>[CH3:14][O:13][C:7]1[CH:6]=[C:5]([C:3]2[N:18]=[C:15]([CH3:16])[S:17][CH:2]=2)[CH:10]=[CH:9][C:8]=1[O:11][CH3:12]

참가 물질

4

반응물 2

HCID 2704232-Bromo-1-(3,4-dimethoxyphenyl)ethan-1-oneHCID 2723949Thioacetamide

생성물 1

HCID 3323984-(3,4-Dimethoxyphenyl)-2-methyl-1,3-thiazole수율 100%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Ex-69A: A solution of 2-bromo-1-(3,4-dimethoxy-phenyl)-ethanone (0.62 g, 2.39 mmol) and thioacetamide (0.18 g, 2.39 mmol) in ethanol (30 mL) was refluxed for 2 hours and the solvent was removed under reduced pressure. The product, 4-(3,4-dimethoxy-phenyl)-2-methyl-thiazole (0.56 g, 100%) was obtained as a white solid and used without further purification. To a suspension of 4-(3,4-dimethoxy-phenyl)-2-methyl-thiazole obtained above (0.70 g, 2.97 mmol) in dichloromethane (60 mL) at 0° C. was added dichloromethyl methyl ether (0.40 mL, 4.46 mmol) followed by addition of titanium tetrachloride (1.0 M solution in dichloromethane, 8.9 mL, 8.9 mmol) dropwise. The reaction mixture was allowed to stir overnight at ambient temperature and then poured into ice. The aqueous solution was extracted with dichloromethane. The solution of dichloromethane was washed with hydrochloric acid (0.5M), saturated solution of sodium bicarbonate and brine, dried over sodium sulfate and concentrated. The product, 2,4-dimethoxy-5-(2-methyl-thiazol-4-yl)-benzaldehyde, was obtained as a white solid. 1H NMR (CDCl3) δ 10.33 (s, 1H), 8.67 (s, 1H), 7.56 (s, 1H), 6.52 (s, 1H), 4.03 (s, 3H), 3.99 (s, 3H), 2.75 (s, 3H).

후처리

  1. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-3354c3f1f1324b749c5386a892babfc9
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

연결된 노트

불러오는 중…