Uses
N,N-Dimethylsulfamide is a byproduct of Tolylfluanide (T536730) fungicide decomposition found in some waters. Upon ozonization it becomes a precursor for carcinogenic Nitrosodimethylamine (N525625). Otherwise N,N-Dimethylsulfamide is a versatile reactant used in various syntheses such as preparation of N-sulfonylbenzaldimines in copper-catalyzed aza-Friedel-Crafts reactions with 1-methylindole.
Synthesis
General procedure for the synthesis of N,N-dimethylsulfonamide from N,N-dimethylaminosulfonyl chloride: N,N-dimethylaminosulfonyl chloride (6.96 mmol, 0.748 mL) was reacted with a methanol solution of 7 N ammonia (104 mmol, 14.92 mL) in a sealed autoclave at 60°C for 16 hours. After completion of the reaction, the solvent was removed from the reaction mixture by evaporation. The resulting solid was suspended in dichloromethane (DCM), filtered and washed with DCM. Subsequently, it was dried under reduced pressure to afford N,N-dimethylsulfonamide (850 mg, yield: 98%), which could be used in subsequent steps without further purification. The product was characterized by 1H NMR (300 MHz, DMSO-d6) with chemical shifts of δ 7.40 (2H, s), 2.38 (6H, s).
References
[1] Patent: WO2013/149997, 2013, A1. Location in patent: Page/Page column 146; 147
[2] Patent: WO2013/102826, 2013, A1. Location in patent: Page/Page column 84
[3] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1980, vol. 19, # 10, p. 935 - 937
[4] Tetrahedron Letters, 2009, vol. 50, # 19, p. 2232 - 2235
[5] Chemische Berichte, 1950, vol. 83, p. 551,554
