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

Participants

Reaction Steps

2-Trifluoromethylpyridine (7 g, 47.6 mmol) in CHCl3 (100 mL) was treated with O-(mesitylenesulfonyl)-N-hydroxylamine (10.2 g, 47.6 mmol) (obtained from treatment of N-tert-butoxycarbonyl-O-(mesitylsulfonyl)hydroxylamine (15 g, 47.6 mmol) with trifluoroacetic acid (35 mL) and stirred at rt under nitrogen. After 16 h a second batch of O-(mesitylenesulfonyl)-N-hydroxylamine (4.8 g, 22.2 mmol) was added and stirring continued for 4 days. Reaction solution was evaporated to dryness, triturated with ether and filtered. Filtrate was washed with ether and dried to yield 1-amino-2-trifluoromethylpyridinium mesitylenesulfonate (9.6 g, 26.5 mmol).

Provenance & Evidence