Benzene → N,N-bis(trimethylsilyl)Methanesulfonamide

HRID 974378Notes

Reaction equation

HRID 974378 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].C(N(CC)CC)C.C1C=CC=CC=1.[CH3:19][Si:20]([CH3:23])([CH3:22])Cl>CCCCCC>[CH3:19][Si:20]([CH3:23])([CH3:22])[N:5]([Si:20]([CH3:23])([CH3:22])[CH3:19])[S:2]([CH3:1])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 72879Methanesulfonamide2×

Product 1

HCID 12503736N,N-bis(trimethylsilyl)Methanesulfonamide

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A glass reactor equipped with a stirrer, nitrogen inlet, reflux condenser and addition funnel was purged with nitrogen and charged with 29.1 g (0.30 mol) of methanesulfonamide, MeSO2NH2, where Me represents the methyl radical, 84.9 ml (0.605 mol) of triethylamine and 240 ml of dry benzene. Trimethylchlorosilane (129.5 ml, 1.00 mol) was then added through the addition funnel over a period of 15 minutes to the stirred mixture, followed by heating at the boiling point for three hours. The mixture was then diluted with 200 ml of hexane and stirring was continued for 30 minutes.

Workup

  1. customA glass reactor equipped with a stirrer, nitrogen inlet
  2. temperaturereflux
  3. additioncondenser and addition funnel
  4. customwas purged with nitrogen
  5. temperatureby heating at the boiling point for three hours

Sources & evidence

ORD record
ord-abc4716cdac84c6f91c8dbce364af083
Source dataset
uspto-grants-1991_11
Patent number
US05068379

Reaction notes

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