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tert-Butyl 4-(chloromethyl)thiazol-2-ylcarbamate synthesis

2synthesis methods
-

Yield:892952-70-4 68%

Reaction Conditions:

Stage #1: 1,3-Dichloroacetone;tert-butyl carbamothioylcarbamate in acetone at 20; for 72 h;
Stage #2: with water;sodium hydrogencarbonate in acetone; for 0.25 h;Product distribution / selectivity;

Steps:

9

Example 9: Preparation of /V-Boc-4-(chIoromethyl)thiazol-2-amine (Intermediate VIII); [0095] To a solution of Intermediate VII (3.0 g, 17 mmol) in acetone (75 mL) was added 1,3-dichloroacetone (2.4 g, 18.7 mmol) at once. The mixture was stirred at room temperature for 72 h. The reaction mixture was treated with NaHCCb (3 g) and stirred for 15 min. The solids were removed by filtration and the filtrate was concentrated in vacuo. Column chromatography (EtOAc/Heptane, 4/1) afforded N-Boc-4-(chloromethyl)thiazol-2- amine (2.9 g, 1 1.6 mmol, 68%) as a white solid.

References:

WO2008/11191,2008,A1 Location in patent:Page/Page column 38