Thiourea → Ethyl 2-amino-4-(5-chloro-2-methoxyphenyl)thiazole-5-carboxylate
Reaction equation
Br[CH:2]([C:8]([C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[O:17][CH3:18])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:19][C:20]([NH2:22])=[S:21]>C(O)C>[NH2:22][C:20]1[S:21][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])[N:19]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of ethyl 2-bromo-3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate (assumed to be 13.2 mmol) and thiourea (1.01 g, 13.3 mmol) in ethanol (25 mL) were heated to reflux for 3 hours, then cooled to room temperature for 18 hours. The resultant solid was removed by filtration and the filtrate evaporated under vacuum. DCM was added to the residue, the organics washed with sodium hydrogen carbonate (sat.aq.), water and brine, and evaporated to dryness. The residue was triturated (DCM) to give ethyl 2-amino-4-(5-chloro-2-methoxyphenyl)thiazole-5-carboxylate (1.30 g, 31%) as a yellow solid. LCMS (method 1) [M+H]+=313.2, RT=3.15 min. 1H NMR (400 MHz, DMSO-d6): δ (ppm) 7.77 (s, br, 2H), 7.39 (dd, 1H), 7.22 (d, 1H), 7.05 (d, 1H), 4.00 (q, 2H), 3.70 (s, 3H), 1.04 (t, 3H).