Ethyl 2-aminothiazole-4-carboxylate → Ethyl 2-imino-3-(2-methoxyethyl)-2,3-dihydro-1,3-thiazole-4-carboxylate hydrobromide

반응식

[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([NH2:11])[S:9][CH:10]=1)=[O:5])[CH3:2].[CH3:12][O:13][CH2:14][CH2:15][Br:16]>>[BrH:16].[NH:11]=[C:8]1[N:7]([CH2:15][CH2:14][O:13][CH3:12])[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:10][S:9]1

참가 물질

반응물 2

HCID 73216Ethyl 2-aminothiazole-4-carboxylate

HCID 809722-Bromoethyl methyl ether

생성물 1

HCID 66860160Ethyl 2-imino-3-(2-methoxyethyl)-2,3-dihydro-1,3-thiazole-4-carboxylate hydrobromide수율 83%

실험 절차

A mixture of 2-aminothiazole-4-carboxylic acid ethyl ester (17.2 g, 100 mmol) and 2-bromoethyl methyl ether (15.3 g, 110 mmol) were processed using the method described in Example 2A to afford 17.1 g (83%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.30 (t, J=7 Hz, 3H) 3.22 (s, 3H) 3.60 (t, J=5 Hz, 2H) 4.32 (t, J=7 Hz, 2H) 4.35-4.61 (m, 2H), 7.84 (s, 1H), 9.76 (s, 1H); MS (DCI/NH3) m/z 231 (M+H)+.

출처 및 근거

ORD 기록: ord-b6053893b56a44448e062a00301c94a6
출처 데이터셋: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08841334B2

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