Hydrochloric Acid → 3-Methylsulfonylamino-4-phenoxyphenol

HRID 1031651Notes

Reaction equation

HRID 1031651 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:15])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1C=CC=CC=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24].Cl>C(Cl)Cl.O>[CH3:22][S:23]([NH:1][C:2]1[CH:3]=[C:4]([OH:15])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:25])=[O:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 135148453-Amino-4-phenoxyphenol

Product 1

HCID 147222673-Methylsulfonylamino-4-phenoxyphenolYield 84.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

20.1 g of 3-amino-4-phenoxyphenol and 23.7 g of pyridine were dissolved in 200 ml of methylene chloride. To the resulting solution being ice-cooled was dropwise added a solution of 12.6 g of methanesulfonyl chloride in 60 ml of methylene chloride, at the same temperature in 30 minutes. The mixture was subjected to reaction at the same temperature for 2 hours. 200 ml of water was added thereto and then 4N hydrochloric acid was added to adjust the pH to 3. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and then dried with anhydrous magnesium sulfate. Thereafter, the organic layer was subjected to distillation under reduced pressure to remove the solvent. The resulting crystal was recrystallized from benzene to obtain 23.7 g (yield: 84.9%) of 3-methylsulfonylamino-4-phenoxyphenol having a melting point of 138°-140° C.

Workup

  1. temperaturecooled
  2. customThe mixture was subjected to reaction at the same temperature for 2 hours
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous sodium chloride solution in this order, and then dried with anhydrous magnesium sulfate
  6. distillationThereafter, the organic layer was subjected to distillation under reduced pressure
  7. customto remove the solvent
  8. customThe resulting crystal was recrystallized from benzene

Sources & evidence

ORD record
ord-d8d5731b58194ebba56b0c59e78a71fe
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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