[CH3:1][C:2]1[S:3][C:4]([CH2:7]O)=[CH:5][N:6]=1.CS(Cl)(=O)=O.C(N(CC)CC)C.[N-:21]=[N+:22]=[N-:23].[Na+]>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[N:21]([CH2:7][C:4]1[S:3][C:2]([CH3:1])=[N:6][CH:5]=1)=[N+:22]=[N-:23]
A solution of (2-methylthiazol-5-yl)methanol (3.99 g, 30.9 mmol) in tetrahydrofuran (100 ml) was cooled to 0° C. and treated with methanesulfonyl chloride (2.40 ml, 30.9 mmol) followed by triethylamine (4.3 ml, 30.9 mmol) added dropwise over 10 min. The resulting mixture was stirred for 20 min, diluted with N,N-dimethylformamide (50 ml) and then treated with sodium azide (3.20 g, 49.2 mmol). After 18 h at 22° C., the reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure followed by chromatography of the residue on silica gel (elution toluene-ethyl acetate 0-20%) gave 4.42 g (92% yield) of the title azide as a clear oil. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.74 (3H, s, CH3), 4.50 (2H, s, CH2), 7.56 (1H, s, CH). MS (ESI+) m/e 155 [M+H+].
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