Ammonia → Methanesulfonamide, N-(trimethylsilyl)-

HRID 435195Notes

Reaction equation

HRID 435195 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[NH:3][Si](C)(C)C.[CH3:10][S:11](N)(=[O:13])=[O:12].N>S1(C2C(=CC=CC=2)C(=O)N1)(=O)=O.C1(C)C=CC=CC=1>[CH3:1][Si:2]([CH3:9])([CH3:8])[NH:3][S:11]([CH3:10])(=[O:13])=[O:12]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 13838HexamethyldisilazaneHCID 72879Methanesulfonamide

Product 1

HCID 11789593Methanesulfonamide, N-(trimethylsilyl)-Yield 127.4%

Reagents, catalysts & solvents 2

HCID 5143SaccharinCatalystHCID 1140TolueneSolvent

Procedure

5.1 ml of hexamethyldisilazane (24.5 mmoles) were added to a refluxing mixture of 3.0 g (31.6 mmoles) of methanesulfonamide, 20 mg (0.11 mmole) of saccharin and 15 ml of toluene while a stream of nitrogen passed over the reaction mixture to expel the ammonia evolved, which was absorbed in water and titrated with 1 N H2SO4. It was found that after refluxing for 20 minutes the calculated amount of ammonia was evolved. The solvent and excess hexamethyldisilazane were evaporated in vacuo and the solid residue was vacuum dried to obtain 5.22 g (99.5%) of N-trimethylsilylmethanesulfonamide melting at 69°-74.5° C. The experiment was repeated without the addition of saccharin and the calculated amount of ammonia was evolved in 35 minutes. Workup as described above yielded 5.25 g (100%) of N-trimethylsilylmethansulfonamide melting at 68°-72.5° C.

Workup

  1. customwhich was absorbed in water
  2. temperaturethat after refluxing for 20 minutes the calculated amount of ammonia
  3. customThe solvent and excess hexamethyldisilazane were evaporated in vacuo
  4. customdried

Sources & evidence

ORD record
ord-f06d69c9bb984d7d9eab77969f504e33
Source dataset
uspto-grants-1983_08
Patent number
US04400509

Reaction notes

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