2-Amino-3-(4-ethoxy-2,4-dioxobutyl)-5-methylthiazol-3-ium bromide → HCID 70817978, 화합물

HRID 82306

반응식

HRID 82306 반응식
[Br-:1].[NH2:2][C:3]1[S:4][C:5]([CH3:17])=[CH:6][N+:7]=1[CH2:8][C:9](=O)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(O)C>[BrH:1].[CH3:17][C:5]1[S:4][C:3]2=[N:2][C:9]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][N:7]2[CH:6]=1

참가 물질

3

반응물 1

HCID 866721332-Amino-3-(4-ethoxy-2,4-dioxobutyl)-5-methylthiazol-3-ium bromide

생성물 1

HCID 70817978HCID 70817978, 화합물수율 97%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Ethyl 4-bromo-3-oxobutanoate (92 g, 0.35 mol) was added to a solution of 5-methylthiazol-2-amine (40 g, 0.35 mol) in acetone (400 mL). The mixture was left to stand overnight and then evaporated to give 2-amino-3-(4-ethoxy-2,4-dioxobutyl)-5-methylthiazol-3-ium bromide in 82% yield, 101 g. 2-amino-3-(4-ethoxy-2,4-dioxobutyl)-5-methylthiazol-3-ium bromide (101 g, 0.28 mol) was then refluxed in ethanol (250 mL) for 2 hours. The solvent was then evaporated to give ethyl 2-(2-methylimidazo[2,1-b]thiazol-6-yl)acetate hydrobromide as yellow crystals in 97% yield, 85 g. Solid K2CO3 was added to a solution of ethyl 2-(2-methylimidazo[2,1-b]thiazol-6-yl)acetate hydrobromide (85 g, 0.28 mol) in water (300 mL) to pH ˜8. The product was extracted with chloroform (3×100 mL), and the combined extracts were dried over Na2SO4 and evaporated to give ethyl 2-(2-methylimidazo[2,1-b]thiazol-6-yl)acetate in 84% yield 52 g. Ethyl 2-(2-methylimidazo[2,1-b]thiazol-6-yl)acetate (52 g, 0.23 mol) was refluxed in 10% aqueous HCl (150 mL) for 2 hours. The solution was evaporated to dryness to give the title compound as brown crystals in 59% yield 32.3 g; m/z 197 [M+H]+.

후처리

  1. customThe solvent was then evaporated

출처 및 근거

ORD 기록
ord-6a1ab516a52c427b9f17a802fb1f353d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

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