Benzyl mercaptan → HCID 18354200, compound

HRID 861296Notes

Reaction equation

HRID 861296 reaction equation
[CH2:1](S)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1>C(#N)C>[CH2:1]([C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 18354200HCID 18354200, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

39.1 g (0.315 mol) of benzylmercaptan are introduced into 200 ml of acetonitrile, 47.8 g (0.346 mol) of K2CO3 are added, and the mixture is stirred for 40 minutes at 60° C. 50.0 g (0.315 mol) of 2-chloro-3-nitropyridine dissolved in 150 ml of acetonitrile are subsequently added dropwise, and the mixture is refluxed for 4 hours. The acetonitrile is distilled off under reduced pressure, the residue is taken up in dichloromethane, the organic phase is washed once using saturated sodium hydrogen carbonate solution and once using 1N hydrochloric acid and dried over magnesium sulfate, the desiccant is filtered off, and the dichloromethane is removed under reduced pressure. Recrystallization from methanol gives 60.9 g (79% of theory) of 2-benzyl-3-nitropyridine of melting point 72° C.

Workup

  1. additionare added
  2. additionare subsequently added dropwise
  3. temperaturethe mixture is refluxed for 4 hours
  4. distillationThe acetonitrile is distilled off under reduced pressure
  5. washthe organic phase is washed once using saturated sodium hydrogen carbonate solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationthe desiccant is filtered off
  8. customthe dichloromethane is removed under reduced pressure
  9. customRecrystallization from methanol

Sources & evidence

ORD record
ord-faee4cc0b5614e76bc4d7f0e95b51dda
Source dataset
uspto-grants-1998_02
Patent number
US05714436

Reaction notes

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