Methanesulfonyl chloride → HCID 14722282, compound

HRID 1031655Notes

Reaction equation

HRID 1031655 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:15][CH3:16])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>N1C=CC=CC=1>[CH3:17][S:18]([NH:1][C:2]1[CH:3]=[C:4]([O:15][CH3:16])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 12459637HCID 12459637, compound

Product 1

HCID 14722282HCID 14722282, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

21.4 g of 3-amino-4-phenylaminoanisole was dissolved in 210 ml of pyridine. The solution was then ice-cooled. Thereto was dropwise added 12 g of methanesulfonyl chloride in 30 minutes. Stirring was conducted for 2 hours at 5°-10° C. The mixture was subjected to distillation under reduced pressure to remove the solvent. To the residue were added 500 ml of water and 300 ml of ethyl acetate. The resulting mixture was adjusted to pH 4 with 4N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The organic layer was then subjected to distillation under reduced pressure to remove the solvent. Toluene was added to the residue, and the resulting crystal was filtered to obtain 23.9 g (yield: 81.8%) of 3-methylsulfonylamino-4-phenylaminoanisole having a melting point of 109°-111° C.

Workup

  1. temperatureice-cooled
  2. customin 30 minutes
  3. distillationThe mixture was subjected to distillation under reduced pressure
  4. customto remove the solvent
  5. additionTo the residue were added 500 ml of water and 300 ml of ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  9. distillationThe organic layer was then subjected to distillation under reduced pressure
  10. customto remove the solvent
  11. additionToluene was added to the residue
  12. filtrationthe resulting crystal was filtered

Sources & evidence

ORD record
ord-f228ca8581d048e3a3651aa0eb52eaa8
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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