Chloroacetaldehyde → (4-Methoxy-phenyl)thiazol-2-yl-amine

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A mixture of (4-methoxy-phenyl)-thiourea (3.0 g, 16.5 mmol) and a 45% aqueous solution of chloroacetaldehyde (12 mL, 82.4 mmol, 5.0 equiv) in EtOH (23 mL) is heated to reflux for 1 h. The resulting dark orange solution is allowed to cool to RT and concentrated in vacuo. NaHCO3 is then added to the oily residue until CO2 evolution subsides and a beige precipitate forms. The product is collected by vacuum filtration, washed thoroughly with water (600 mL), and dried in vacuo. Title compound: ES-MS: 207.0 [M+H]+; single peak at tR=5.32 min (System 1); Rf=0.17 (CH2Cl2/MeOH, 95/5).

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