Water → 4-((methylthio)methyl)benzonitrile(WX192182)

HRID 1421553Notes

Reaction equation

HRID 1421553 reaction equation
C(#N)C.[C:4]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10]Br)=[CH:8][CH:7]=1)#[N:5].[Na].[CH3:15][SH:16].O>C1(C)C=CC=CC=1>[CH3:15][S:16][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([C:4]#[N:5])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 869964-(Bromomethyl)benzonitrileHCID 45051789Methylmercaptan sodium

Product 1

HCID 206497164-((methylthio)methyl)benzonitrile(WX192182)

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To an acetonitrile solution (500 ml) of 4-cyanobenzyl bromide (50 g), 15% methyl mercaptan sodium salt (120 ml) was added at a room temperature and heated for 6 hours with refluxing. After cooling to a room temperature, water (1 l) and toluene (1 l) was added thereto. The organic layer was separated and washed successively with an aqueous 2N sodium hydroxide solution sulfate. After distilling off the solvent, 4-methylmercaptomethylbenzonitrile (38 g) was obtained.

Workup

  1. temperatureheated for 6 hours
  2. temperaturewith refluxing
  3. customThe organic layer was separated
  4. washwashed successively with an aqueous 2N sodium hydroxide solution sulfate
  5. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-4244a8160d83451cabf1a5ebea20c65c
Source dataset
uspto-grants-2000_06
Patent number
US06077866

Reaction notes

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