Ethanethiol → HCID 14722283, compound

HRID 1031656Notes

Reaction equation

HRID 1031656 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]([O:19]C)[CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:4])=[O:3].C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]([OH:19])[CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 14722282HCID 14722282, compound

Product 1

HCID 14722283HCID 14722283, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

29.2 g of 3-methylsulfonylamino-4-phenylaminoanisole, 18.6 g of ethanethiol and 300 ml of methylene chloride were mixed and then ice-cooled. To the mixture was added 40 g of aluminum chloride in 20 minutes. Stirring was conducted for 3 hours at 5°-10° C. The reaction mixture was introduced into 500 ml of ice water. The resulting organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order and then dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. Ethanol was added to the residue and the resulting crystal was filtered to obtain 23.9 g (yield: 86%) of 3-methylsulfonylamino-4-phenylaminophenol having a melting point of 184°-186° C. IR (KBr) cm-1 : 3425, 3380, 3250, 1600, 1490, 1310, 1150

Workup

  1. temperatureice-cooled
  2. customThe resulting organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated aqueous sodium chloride solution in this order and then dried with anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. additionEthanol was added to the residue
  7. filtrationthe resulting crystal was filtered

Sources & evidence

ORD record
ord-26d481bca4d9447e8e938d4d3977b267
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

Loading…