Methanethiol → 2-(Methylthio)benzonitrile

HRID 2405025Notes

Reaction equation

HRID 2405025 reaction equation
Cl[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Na].[CH3:11][SH:12]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClC1C=CC=CC=1>[CH3:11][S:12][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 878MethanethiolHCID 133912-ChlorobenzonitrileHCID 5360545Sodium

Product 1

HCID 1387812-(Methylthio)benzonitrile

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 7964ChlorobenzeneSolvent

Procedure

2-Chlorobenzonitrile (27.5 g, 0.2 mol), monochlorobenzene (30.0 g), and a 50% by weight aqueous solution (1.0 g) of tetra-n-butyl ammonium bromide were placed in a 500-ml four-necked flask equipped with a stirrer, a thermometer, a dropping funnel, and a condenser under a nitrogen atmosphere to obtain a mixture. A 30% by weight aqueous solution (51.4 g) of sodium salt of methanethiol (0.22 mol) was added dropwise to the mixture at 60 to 65° C. over a period of 5 hours under stirring. After completion of the dropwise addition, the mixture was further allowed to react at the same temperature for 12 hours. By this operation, 2-(methylthio)benzonitrile was obtained.

Workup

  1. customequipped with a stirrer
  2. customa thermometer, a dropping funnel, and a condenser under a nitrogen atmosphere to obtain a mixture
  3. additionAfter completion of the dropwise addition
  4. customto react at the same temperature for 12 hours

Sources & evidence

ORD record
ord-f37bfa961c5648ed9ed683c9f58b3d3c
Source dataset
uspto-grants-2014_08
Patent number
US08802862B2

Reaction notes

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