Water → HCID 21057621, compound

Participants

Reaction Steps

Lithium bis(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran, 3.3 ml, 0.0033 mol) was added dropwise to a solution of N-(4-chloro-3-methylisothiazol-5-yl)-(2-propylbenzotriazol-5-yl)acetamide (Compound No. A3.1) (0.699 g, 0.002 mol) in tetrahydrofuran (10 ml) and once the addition was complete the mixture was stirred at room temperature for 30 minutes. Chloromethylethyl ether (0.620 g, 0.0066 mol) was added and the mixture was stirred at room temperature for 2 hours. The mixture was poured into water, neutralised, and extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was further purified by flash column chromatography, eluting initially with 2:1 hexane:ethyl acetate and then with ethyl acetate to give N-(4-chloro-3-methylisothiazol-5-yl)-N-(ethoxymethyl)-(2-propylbenzotriazol-5-yl)acetamide (0.135 g) as an orange gum and N-[2-ethoxymethyl-4-chloro-3-methylisothiazolin-5-ylidene]-(2-propylbenzotriazol-5-yl)-acetamide (0.128 g) as a colourless solid, m.p. 108–109° C.

Provenance & Evidence