Triethylamine → 1,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-mesitylene sulphonyl chloride (2.0 g, 9.14 mmol) in dry THF (50 mL), is added N-Boc-hydroxylamine (1.21 g, 9.14 mmol) and cooled to 0° C. under N2 atmosphere. The reaction mixture is stirred for 5 minutes. To this mixture triethylamine (1.1 g, 11 mmol) is added slowly over 10 minutes. The reaction mixture is stirred for 1 hour at 0° C. and upon completion, the solvent removed in vacuo. The residue is redissolved in dichloromethane (50 mL) and washed with water (2×50 mL), 10% aqueous NaHCO3 (50 mL) and dried over MgSO4. It is then concentrated under reduced pressure at room temperature to get the product as an off white solid; (2.1 g, 73%). TLC: pet ether/ethyl acetate (8/2) Rf—0.4. 1H NMR (DMSO-d6; 400 MHz): δ 11.16 (s, 1H), 7.12 (s, 2H), 2.49 (s, 6H), 2.28 (s, 3H), 1.23 (s, 9H).

Provenance & Evidence