4-Fluorobenzenesulfonyl chloride → 4-Fluoro-N-(trimethylsilyl)benzene-1-sulfonamide

HRID 1613843Notes

Reaction equation

HRID 1613843 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][Si:13]([CH3:20])([CH3:19])[NH:14][Si](C)(C)C>>[CH3:12][Si:13]([CH3:20])([CH3:19])[NH:14][S:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

3

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 13838Hexamethyldisilazane

Product 1

HCID 149491894-Fluoro-N-(trimethylsilyl)benzene-1-sulfonamide

Conditions

Temperature
115 °C

Procedure

A glass reactor equipped with a stirrer, reflux condenser and gas inlet was charged with solid 4-fluorobenzenesulfonyl chloride 0.250 mol, 49.65 g). Hexamethyldisilazane (0.263 mol, 56.6 ml) was added to the reactor and the mixture was gradually heated with stirring to a temperature of 115° C., at which time it became clear. The mixture was then heated at the boiling point for 21 hours. Analysis of the mixture by 1H NMR indicated that the reaction was about 50% complete. Volatile materials were then removed by heating at a temperature of 65° C. under reduced pressure to yield a brown liquid which was distilled to remove unreacted sulfonyl chloride. The residue was redistilled under a pressure of 0.03 mm. Hg. The fraction collected from 40° to 97° C. was analyzed by 1H NMR and was found to contain the N-mono- and N,N-bis(trimethylsilyl)sulfonamides in a 1:1 molar ratio. Using the same analytical technique a second fraction collected within the range from 97° and 122° C. was found to contain the N-mono- and N,N-bis(trimethylsilyl)sulfonamides in a 8.5:1 molar ratio. The second fraction was used as the starting material (3c) for the subsequent reaction.

Workup

  1. customA glass reactor equipped with a stirrer
  2. temperaturereflux condenser and gas inlet
  3. temperaturethe mixture was gradually heated
  4. temperatureThe mixture was then heated at the boiling point for 21 hours
  5. customVolatile materials were then removed
  6. temperatureby heating at a temperature of 65° C. under reduced pressure
  7. customto yield a brown liquid which
  8. distillationwas distilled
  9. customto remove unreacted sulfonyl chloride
  10. distillationThe residue was redistilled under a pressure of 0.03 mm. Hg
  11. customThe fraction collected from 40° to 97° C.
  12. customcollected within the range from 97° and 122° C.
  13. customThe second fraction was used as the starting material (3c) for the subsequent reaction

Sources & evidence

ORD record
ord-15afd934d4d74cf88fa5e0b2b616700f
Source dataset
uspto-grants-1993_03
Patent number
US05194557

Reaction notes

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