4-Methoxy-alpha-toluenethiol → 4-Cyano-3-(4-methoxyphenyl)methylmercaptopyridine

HRID 1200010Notes

Reaction equation

HRID 1200010 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][SH:8])=[CH:5][CH:4]=1.Cl[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C:18]#[N:19]>C[O-].[Na+].CO.C(#N)C>[C:18]([C:17]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[S:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)#[N:19]

Participants

6

Reactant 2

HCID 804074-Methoxy-alpha-toluenethiolHCID 106783063-Chloropyridine-4-carbonitrile

Product 1

HCID 142776484-Cyano-3-(4-methoxyphenyl)methylmercaptopyridineYield 60%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 10942334Sodium MethoxideSolvent

Procedure

A solution of 6.2 g (40 mmol) of p-methoxybenzylmercaptan in 9.8 mL of 4.4M sodium methoxide in methanol was added dropwise to a solution of 5.52 g (40 mmol) of 3-chloro-4-cyanopyridine in dry acetonitrile that has been cooled in an ice bath. After addition was complete the solution was allowed to warm to room temperature over 2 hours. The solvent was concentrated and the residue was partitioned between dichloromethane and water. The aqueous layer was extracted with two portions of dichloromethane and the combined extracts were washed with brine, dried (MgSO4) and concentrated to afford 6.1 g (60%) of a pale yellow crystalline solid, m.p. 80°-81° C.

Workup

  1. temperaturehas been cooled in an ice bath
  2. additionAfter addition
  3. concentrationThe solvent was concentrated
  4. customthe residue was partitioned between dichloromethane and water
  5. extractionThe aqueous layer was extracted with two portions of dichloromethane
  6. washthe combined extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-347ca1233e97461c9fdc3a9bc09ef488
Source dataset
uspto-grants-1990_02
Patent number
US04904672

Reaction notes

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