Synthesis
A solution of 2-nitrobenzene-1-sulfonyl chloride (500 g, 2.26 mol) in pyridine (1500 mL) was slowly added dropwise to a solution of O-benzylhydroxylamine hydrochloride (400 g, 2.51 mol) in pyridine (1500 mL) at 0 °C. The reaction mixture was then stirred at 20 °C overnight. After completion of the reaction, the mixture was concentrated under reduced pressure, diluted with dichloromethane (DCM) and washed three times with 10% hydrochloric acid solution. After combining the organic layers, the mixture was again concentrated under reduced pressure and recrystallized by dichloromethane to give N-(benzyloxy)-2-nitrobenzenesulfonamide as a yellow solid (485 g, 62.6% yield).
References
[1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8081 - 8086
[2] Synthesis, 2001, # 7, p. 1086 - 1092
[3] Journal of Organic Chemistry, 2015, vol. 80, # 12, p. 6076 - 6082
[4] Patent: US2013/289012, 2013, A1. Location in patent: Paragraph 0199; 0200
[5] Patent: US2013/296555, 2013, A1. Location in patent: Paragraph 0231; 0232
