3,3-Dimethyl-2-nitroso-2,3-dihydrobenzo[d]isothiazole 1,1-Dioxide

• Morpholine [M0465]
• 3,3-Dimethyl-2-nitroso-2,3-dihydrobenzo[d]isothiazole 1,1-Dioxide [D6544]
• Dichloromethane

Morpholine (50.3 mg, 0.58 mmol) and 3,3-dimethyl-2-nitroso-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide (174 mg, 0.69 mmol, 1.2 eq.) were dissolved in dichloromethane (5.8 mL) and the mixture was stirred at room temperature for 4 hours. The solution was then concentrated under reduced pressure. The crude product was purified by silica gel chromatography (dichloromethane: hexane = 1:1 - 7:3) to afford N-nitrosomorpholine (57.8 mg, 86% yield) as a clear yellow oil.

The reaction mixture was monitored by TLC (hexane:EtOAc = 2:1, Rf = 0.25) and NMR

N-Nitrosomorpholine

¹H NMR (270 MHz, CDCl₃); δ 4.29 (t, J = 4.9 Hz, 2H), 3.90-3.84 (m, 4H), 3.65 (t, J = 3.9 Hz, 2H).

• Versatile New Reagent for Nitrosation under Mild Conditions
  • J. D. Galloway, C. Sarabia, J. C. Fettinger, H. P. Hratchian, R. D. Baxter, Org. Lett. 2021, 23, 3253.