Dimethylamine → 4-fluoro-N,N-dimethylbenzenesulfonamide

HRID 371476Notes

Reaction equation

HRID 371476 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][NH:13][CH3:14]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:13]([CH3:14])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 95884-Fluorobenzenesulfonyl chloride

Product 1

HCID 7993014-fluoro-N,N-dimethylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 38.9 g (0.20 mole) of 4-fluorobenzenesulfonylchloride in 20 ml of methylene chloride was added slowly to 300 ml of a 40% aqueous dimethylamine solution during 0.5 hour period. The reaction was exothermic. After the reaction mixture was cooled a yellow solid was precipitated. The solid was collected, dissolved in 300 ml of ethyl acetate, and dried over magnesium sulfate. The solution was concentrated to 100 ml and a light yellow crystal formed. The crystal was collected and air-dried to afford 39 g of the product, mp 40°-43° C.

Workup

  1. temperatureAfter the reaction mixture was cooled a yellow solid
  2. customwas precipitated
  3. customThe solid was collected
  4. dissolutiondissolved in 300 ml of ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solution was concentrated to 100 ml
  7. customa light yellow crystal formed
  8. customThe crystal was collected
  9. customair-dried

Sources & evidence

ORD record
ord-50892e292b354823bf6126a20a71ccd5
Source dataset
uspto-grants-1985_07
Patent number
US04532240

Reaction notes

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