(2-Methoxyethyl)thiourea → 2-[2-(2-Methoxy-ethylamino)-5-methyl-thiazol-4-yl]ethanol

HRID 1597450Notes

Reaction equation

HRID 1597450 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]([NH2:8])=[S:7].Br[CH:10]([CH3:18])[C:11](=O)[CH2:12][C:13](OC)=[O:14]>C(Cl)(Cl)Cl.CO>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[S:7][C:10]([CH3:18])=[C:11]([CH2:12][CH2:13][OH:14])[N:8]=1

Participants

4

Reactant 2

HCID 1810725(2-Methoxyethyl)thioureaHCID 9815681Methyl 4-bromo-3-oxopentanoate

Product 1

HCID 107512152-[2-(2-Methoxy-ethylamino)-5-methyl-thiazol-4-yl]ethanolYield 66.2%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

The title compound (800 mg) was prepared from 750 mg (5.59 mmol) of 2-methoxyethyl thiourea and 1.17 g (5.59 mmol) of methyl 4-bromo-3-oxo-pentanoate according to the method of Intermediate 60, followed by the procedure outlined for the preparation of Intermediate 43 nd purification via silica gel flash column chromatography using chloroform/MeOH 9/1 as eluent: 1H NMR (CDCl3, 400 MHz) δ 3.82 (t, 2H, J=5.5), 3.58 (t, 2H, J=6.9), 3.41 (m, 2H), 3.36 (s, 3H), 2.65 (t, 2H, J=6.9), 2.19 (s, 3H).

Sources & evidence

ORD record
ord-377cf1de60874b5c9858ff760b3d3b81
Source dataset
uspto-grants-2001_09
Patent number
US06294580B1

Reaction notes

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