Ethanethiol → HCID 14722280, compound

HRID 1031653Notes

Reaction equation

HRID 1031653 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][C:9]=1[NH:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1[NH:16][S:17]([C:20]([F:23])([F:21])[F:22])(=[O:19])=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 14722279HCID 14722279, compound

Product 1

HCID 14722280HCID 14722280, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

34.7 g of 4-phenoxy-3-trifluoromethylsulfonylaminoanisole and 31 g of ethanethiol were dissolved in 350 ml of methylene chloride. The resulting solution was then ice-cooled. Thereto was added 27 g of aluminum chloride at the same temperature in 30 minutes. Stirring was conducted for 30 minutes at 5°-10° C. The reaction mixture was poured into 300 ml of ice water and the resulting organic layer was separated. The organic layer was washed with water and a saturated aqueous sodium chloride solution in this order, dried with anhydrous magnesium sulfate, and subjected to distillation under reduced pressure to remove the solvent. The resulting crystal was recrystallized from toluene to obtain 28.5 g (yield: 85.6%) of 4-phenoxy-3-trifluoromethylsulfonylaminophenol having a melting point of 97°-99° C.

Workup

  1. temperatureice-cooled
  2. customthe resulting organic layer was separated
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution in this order, dried with anhydrous magnesium sulfate
  5. distillationsubjected to distillation under reduced pressure
  6. customto remove the solvent
  7. customThe resulting crystal was recrystallized from toluene

Sources & evidence

ORD record
ord-1b3ca6037d8d4601b2407a2f557afd5a
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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