HCID 14255266, compound → HCID 14365373, compound

HRID 1111527Notes

Reaction equation

HRID 1111527 reaction equation
[S:1]([O-])(O)=O.[Na+].[CH2:6]([S:11]([C:14]1[CH:19]=[CH:18][C:17](Cl)=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:7]([CH3:10])([CH3:9])[CH3:8]>CN1CCCC1=O>[CH2:6]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([SH:1])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 14255266HCID 14255266, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 14365373HCID 14365373, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

14.4 g (0.194 mol) of sodium hydrogen sulphite (NaSH·H2O) in 120 ml of N-methylpyrrolidone are introduced and the water is removed at 160° C. with nitrogen. The mixture is cooled to 100° C., 20 g (0.081 mol) of 4-(neopentylsul-phonyl)-chlorobenzene are added, and the mixture is further reacted at 125° C. for 5 hours and the solvent is distilled off under reduced pressure. The residue is dissolved in 150 ml of water and acidified at 10°-20° C. with half-concentrated hydrochloric acid. The mixture is extracted with 100 ml of methylene chloride, the organic phase is washed neutral with water, dried with magnesium sulphate, concentrated and, after addition of 50 ml of toluene, distilled at 0.1 mbar up to an inside temperature of 130° C. to give 19 g of 4-(neopentylsulphonyl)-thiophenol of boiling point: 130° C./0.1 mbar; purity by gas chromatography: 98.6%=95% of theory.

Workup

  1. customthe water is removed at 160° C. with nitrogen
  2. customthe mixture is further reacted at 125° C. for 5 hours
  3. distillationthe solvent is distilled off under reduced pressure
  4. dissolutionThe residue is dissolved in 150 ml of water
  5. customacidified at 10°-20° C. with half-concentrated hydrochloric acid
  6. extractionThe mixture is extracted with 100 ml of methylene chloride
  7. washthe organic phase is washed neutral with water
  8. dry with materialdried with magnesium sulphate
  9. concentrationconcentrated
  10. additionafter addition of 50 ml of toluene
  11. distillationdistilled at 0.1 mbar up to an inside temperature of 130° C.

Sources & evidence

ORD record
ord-42ff1a64b5af4027bb19883975541bbd
Source dataset
uspto-grants-1990_12
Patent number
US04980510

Reaction notes

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