Methyl 5-(propan-2-yl)-1,3-thiazole-4-carboxylate synthesis
- Product Name:Methyl 5-(propan-2-yl)-1,3-thiazole-4-carboxylate
- CAS Number:81569-26-8
- Molecular formula:C8H11NO2S
- Molecular Weight:185.24
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Yield:-
Reaction Conditions:
Stage #1: methyl 2-amino-5-isopropyl-1,3-thiazole-4-carboxylatewith hypophosphorous acid;sodium nitrite at -5 - 0;
Stage #2: with sodium hydroxide in water;
Stage #3: with sodium hydrogencarbonate in water;
Steps:
70
Intermediate 70Methyl 5-(1 -methylethyl)-1 ,3-thiazole-4-carboxylate To a solution of methyl 2-amino-5-(1-methylethyl)-1 ,3-thiazole-4-carboxylate (2.15g) (available from ABCR) in 30% hypophosphorus acid (53ml) at -5°C was added, slowly beneath the surface, maintaining the temperature between -5 and O0C, sodium nitrite (1.6g) and the mixture was stirred for a further 1 h at O0C. The cooling bath was removed for 2h, then replaced while a cool solution of sodium hydroxide (8.5g) in water (100ml) added slowly. The solution was neutralised by the addition of solid sodium hydrogencarbonate and extracted with diethyl ether (50ml), then dried over sodium sulphate. The mixture was evaporated and purified by chromatography on silica gel eluting with a gradient of ethyl acetate in cyclohexane to give the title compound (1.9g) as a yellow oil. LC/MS R1 2.1 min m/z 186 [MH+]. Method C
References:
WO2009/147188,2009,A1 Location in patent:Page/Page column 119
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