Methyl dichloroacetate → 2-Amino-5-(2-(3-chlorophenyl)ethyl)-4-thiazolecarboxylic acid, methyl ester

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Reaction Steps

A solution of sodium methoxide (made from 1.43 g of sodium in dry methanol (20 ml) was added dropwise to a stirred solution of 2-(3-chlorophenyl)propanal (10.4 g) and methyl dichloroacetate (6.4 ml) in diethyl ether (30 ml) at 0° C. under nitrogen. After 1 h the mixture was quenched with brine and the product extracted into diethyl ether. The organic phase was collected, dried (MgSO4) and evaporated under reduced pressure to leave a yellow oil. The oil and thiourea (4.72 g) were dissolved in methanol (40 ml) and the mixture set at reflux for 4 h. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was separated, washed with water, collected, dried (MgSO4) and solvent evaporated under reduced pressure to leave a brown solid. The solid was triturated with isohexane and ethyl acetate mixtures and filtered to leave the subtitle product.

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