Benzyl mercaptan → HCID 22674073, compound

HRID 1173115Notes

Reaction equation

HRID 1173115 reaction equation
[H-].[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 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22674196HCID 22674196, compound

Product 1

HCID 22674073HCID 22674073, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

843 mg (21 mmol, 55% oily) of sodium hydride was suspended in dimethyl sulfoxide (30 ml). Under ice-cooling, 2.0 ml (16.7 mmol) of benzylmercaptan was added thereto, 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. temperatureUnder ice-cooling
  2. stirringby stirring at room temperature overnight
  3. extractionby extracting with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThen, the residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-667831f268894b0ba3095629353a8978
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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