Benzene → N,N-bis(trimethylsilyl)Methanesulfonamide

HRID 2253844Notes

Reaction equation

HRID 2253844 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-7b16e3920e764b589a77fe11b708ebf9
Source dataset
uspto-grants-1993_08
Patent number
US05233019

Reaction notes

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