3-Chlorophenol → HCID 53787299, compound

HRID 327744Notes

Reaction equation

HRID 327744 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH3:9][N:10]([CH3:15])[S:11](Cl)(=[O:13])=[O:12].[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([O:8][S:11](=[O:13])(=[O:12])[N:10]([CH3:15])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 79333-ChlorophenolHCID 14798Sodium HydroxideHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 53787299HCID 53787299, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 25.7 g (0.2 mole) of 3-chlorophenol and 34.9 g (0.24 mole) of dimethylsulfamoyl chloride (Aldrich) in 150 ml of toluene was stirred and heated at reflux for 16 h, cooled and treated with 300 ml of 15% sodium hydroxide solution. The layers were separated and the organic layer was washed with two 200 ml portions of 15% sodium hydroxide solution, 300 ml of water and dried (magnesium sulfate). The solvent was evaporated under reduced pressure and the brown viscous oil was purified by chromatography (4.5×90 in glass column, 530 g of silica gel, ethyl acetate-hexanes, 1:6). Fractions containing the desired product were combined and the solvents were evaporated under reduced pressure to yield 10.5 g (47%) of the title compound as a light yellow liquid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 h
  3. temperaturecooled
  4. customThe layers were separated
  5. washthe organic layer was washed with two 200 ml portions of 15% sodium hydroxide solution, 300 ml of water
  6. dry with materialdried (magnesium sulfate)
  7. customThe solvent was evaporated under reduced pressure
  8. customthe brown viscous oil was purified by chromatography (4.5×90 in glass column, 530 g of silica gel, ethyl acetate-hexanes, 1:6)
  9. additionFractions containing the desired product
  10. customthe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-0cc2b03be6744fc8b0a721504453a1d9
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

Loading…