Benzyl mercaptan → 5-(Benzylsulfanyl)-1,3-dimethyl-4-nitro-1H-pyrazole

HRID 1031337Notes

Reaction equation

HRID 1031337 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O-].[Na+].Cl[C:13]1[C:14]([N+:20]([O-:22])=[O:21])=[C:15]([CH3:19])[N:16](C)[N:17]=1>CN(C=O)C>[CH2:1]([S:8][C:13]1[N:17]([CH3:9])[N:16]=[C:15]([CH3:19])[C:14]=1[N+:20]([O-:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 10942334Sodium MethoxideHCID 22167583HCID 22167583, compound

Product 1

HCID 144611035-(Benzylsulfanyl)-1,3-dimethyl-4-nitro-1H-pyrazoleYield 84.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzylmercaptan (50.8 g) (0.41 mol) was added to 21 g of sodium methoxide in 480 ml of DMF under ice-cooling and then 65.2 g (0.37 ml) of 5-chloro-2,3-dimethyl-4-nitropyrazole was added. After stirring at room temperature for 3 hr., DMF was evaporated under reduced pressure, and the residue was diluted with ice-water. The precipitated solids were filtered, washed with water and further with n-hexane and dried to give 82.4 g of the title compound. m.p. 82 -83° C.

Workup

  1. temperaturecooling
  2. custom, DMF was evaporated under reduced pressure
  3. additionthe residue was diluted with ice-water
  4. filtrationThe precipitated solids were filtered
  5. washwashed with water and further with n-hexane
  6. customdried

Sources & evidence

ORD record
ord-1af5bebd16bd4766b30dc9411a62d40f
Source dataset
uspto-grants-1990_09
Patent number
US04954164

Reaction notes

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