N-(diphenylphosphoryl)-P,P-diphenylphosphinic amide synthesis
- Product Name:N-(diphenylphosphoryl)-P,P-diphenylphosphinic amide
- CAS Number:31239-06-2
- Molecular formula:C24H21NO2P2
- Molecular Weight:417.38
Yield:31239-06-2 67.1%
Reaction Conditions:
Stage #1: diphenylphosphinamidewith sodium hydride in tetrahydrofuran;mineral oil at 0; for 0.5 h;Inert atmosphere;
Stage #2: Diphenylphosphinic chloride in tetrahydrofuran;mineral oil at 0 - 20;Inert atmosphere;
Steps:
General and typical procedure for the synthesis of N-(diphenylphosphoryl)-4-methylbenzenesulfonamide 10a
General procedure: A slurry of P,P-diphenylphosphinic amide (1.0 g, 4.6 mmoL) in THF (20 mL) at 0 C was added NaH (0.5 g, 60% on oil, 12.5 mmol) and the mixture was stirred for 30 min. Then TsCl (1.3 g, 6.9 mmol) was added and the mixture was stirred and the reaction mixture was warmed slowly to ambient temperature and stirred overnight. Water was added to quench the reaction and reaction mixture was extracted with DCM. The organic solvent was concentrated and residue was purified on column eluted with EtOAc/MeOH (100:0 to 100:5, v/v) to yield 1.2 g 10a as a whilte solid in 70% yield. 1H NMR (400 MHz, DMSO-d6): δ 7.79-7.67 (m, 6H), 7.61-7.55 (m, 2H), 7.53-7.46 (m, 4H), 7.36 (d, J = 8.0 Hz, 2H), 2.39 (s, 3H); 13C NMR (100 MHz, DMSO-d6): δ 142.77, 139.95, 132.87, 132.08, 132.05, 131.58, 131.36, 131.26, 129.20, 128.52, 128.39, 126.47, 20.96; 31P NMR (162 MHz, DMSO-d6): δ 16.13; MS: calculates for C19H19NO3PS [M + H]: 372.08; found: 372.06.
References:
Han, Zhengxu S.;Wu, Hao;Qu, Bo;Wang, Yuwen;Wu, Ling;Zhang, Li;Xu, Yibo;Wu, Linglin;Zhang, Yongda;Lee, Heewon;Roschangar, Frank;Song, Jeff J.;Senanayake, Chris H. [Tetrahedron Letters,2019,vol. 60,# 28,p. 1834 - 1837] Location in patent:supporting information
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