Benzyl mercaptan → HCID 22674073, compound

HRID 1005672Notes

Reaction equation

HRID 1005672 reaction equation
[OH-].[Na+].[CH2:3]([SH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][NH:16][N:15](Cl)[CH:14]=1.[Cl-].[NH4+]>CS(C)=O>[CH2:3]([S:10][N:15]1[CH:14]=[C:13]([O:12][CH3:11])[CH:18]=[CH:17][NH:16]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 7509Benzyl mercaptanHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 22674196HCID 22674196, compound

Product 1

HCID 22674073HCID 22674073, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In dimethyl sulfoxide (30 ml) was suspended 843 mg (21 mmol, 55% in oil) of sodium hydroxide, and 2.0 ml (16.7 mol) of benzylmercaptan was added thereto under ice-cooling, followed by stirring for 10 minutes. To the reaction mixture was added 2.5 g (17.6 mmol) of 4-methoxy-2-chloropyridazine, followed by stirring at room temperature overnight. To the reaction mixture was added an aqueous saturated ammonium chloride, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. Then, the residue was purified by silica gel chromatography, to give 1.63 g of the title compound.

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. stirringby stirring at room temperature overnight
  4. extractionby extracting with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThen, the residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-87f008bffb15491b83af258dd3fe7282
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

Loading…