Water → HCID 13712178, compound

HRID 414048Notes

Reaction equation

HRID 414048 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][CH2:14][CH2:15][NH:16][CH3:17].C(=O)([O-])[O-].[Na+].[Na+].O>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:13]([CH3:12])[CH2:14][CH2:15][NH:16][CH3:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8070N,N'-DimethylethylenediamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 10340Sodium Carbonate

Product 1

HCID 13712178HCID 13712178, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent4×

Procedure

A solution of 4-fluorobenzenesulphonyl chloride (6.0 g) in chloroform (30 ml) was added dropwise to a well-stirred solution of N,N'-dimethyl-ethylenediamine (25 g) in chloroform (300 ml) at room temperature. After 2 hours the chloroform solution was vigorously shaken with aqueous sodium carbonate solution, separated, dried (MgSO4) and evaporated under reduced pressure to give an oil. The oil was treated with chloroform (60 ml) and water (100 ml). The two solvents were mixed thoroughly and were then separated. The chloroform layer was dried (MgSO4) and evaporated under reduced pressure to give an oil. Final traces of N,N'-dimethyl-ethylenediamine were removed by heating the oil under low vacuum to give 4-fluoro-N-methyl-N-[2-(methylamino)ethyl]benzenesulphonamide.

Workup

  1. customseparated
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customto give an oil
  5. additionThe two solvents were mixed thoroughly
  6. customwere then separated
  7. dry with materialThe chloroform layer was dried (MgSO4)
  8. customevaporated under reduced pressure
  9. customto give an oil
  10. customFinal traces of N,N'-dimethyl-ethylenediamine were removed
  11. temperatureby heating the oil under low vacuum

Sources & evidence

ORD record
ord-462fd15b02c54a828f05357b256871a0
Source dataset
uspto-grants-1988_12
Patent number
US04789677

Reaction notes

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