2-Bromoethyl methyl ether → Ethyl [2-imino-3-(2-methoxyethyl)-2,3-dihydro-1,3-thiazol-4-yl]acetate hydrobromide

HRID 78399

Reaction equation

HRID 78399 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6]1[N:7]=[C:8]([NH2:11])[S:9][CH:10]=1)[CH3:2].[CH3:13][O:14][CH2:15][CH2:16][Br:17]>>[BrH:17].[CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6]1[N:7]([CH2:16][CH2:15][O:14][CH3:13])[C:8](=[NH:11])[S:9][CH:10]=1)[CH3:2]

Participants

3

Reactant 2

HCID 809722-Bromoethyl methyl etherHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl ester

Product 1

HCID 86618901Ethyl [2-imino-3-(2-methoxyethyl)-2,3-dihydro-1,3-thiazol-4-yl]acetate hydrobromideYield 83%

Procedure

A mixture of (2-aminothiazol-4-yl)acetic acid ethyl ester (18.6 g, 100 mmol) and 2-bromoethyl methyl ether (15.3 g, 110 mmol) were processed using the method described in Example 2A to afford 14.1 g (83%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.14-1.28 (m, 3H) 3.24 (s, 3H) 3.54 (t, J=5 Hz, 2H) 3.91 (s, 2H) 4.04-4.25 (m, 4H) 6.92 (s, 1H) 9.50 (s, 1H); MS (DCI/NH3) m/z 231 (M+H)+.

Sources & evidence

ORD record
ord-85650a6abad9497b9243630e4d36361d
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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