4-(Methoxymethyl)-1,3-thiazol-2-amine synthesis
- Product Name:4-(Methoxymethyl)-1,3-thiazol-2-amine
- CAS Number:640768-40-7
- Molecular formula:C5H8N2OS
- Molecular Weight:144.19
67-56-1
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Yield:640768-40-7 43%
Reaction Conditions:
Stage #1: 1,1-Dichloroacetone;thiourea at 55; for 3 h;
Stage #2: methanolwith magnesium sulfate for 72 h;Heating / reflux;
Steps:
2 Manufacture of 2-amino-4-methoxymethylthiazole
Reference Example 2 Manufacture of 2-amino-4-methoxymethylthiazole To a solution (120 ml) of 13.4 g (106 mmol) of dichloroacetone were added 8.06 g (106 mmol) of thiourea followed by stirring at 55°C for 3 hours. The reaction solution was concentrated and 200 ml of methanol and 15.1 g (125 mmol) of magnesium sulfate were added to the resulting white solid followed by heating to reflux for 3 days. The reaction mixture was filtered through Celite and the filtrate was concentrated and partitioned by chloroform and a saturated aqueous solution of sodium hydrogen carbonate. After the organic layer was dried and concentrated, the resulting residue was purified by a silica gel column chromatography (ethyl acetate) and by crystallization from a mixed solvent of hexane and ethyl acetate (4:1) to give 6.59 g (yield: 43%) of the title compound as a yellow solid.1H-NMR (CDCl3) δ: 3.44 (3H, s), 4.34 (2H, s), 6.45 (1H, s) ESI-MS (m/e): 145 [M+H]+
References:
EP1598349,2005,A1 Location in patent:Page/Page column 126
