Water → 5-Chloro-2-(methylthio)benzonitrile

HRID 1013953Notes

Reaction equation

HRID 1013953 reaction equation
[Na].[CH3:2][SH:3].[Cl:4][C:5]1[CH:6]=[CH:7][C:8](F)=[C:9]([CH:12]=1)[C:10]#[N:11].O>CS(C)=O>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([S:3][CH3:2])=[C:9]([CH:12]=1)[C:10]#[N:11]

Participants

5

Reactant 3

HCID 962WaterHCID 936535-Chloro-2-fluorobenzonitrileHCID 45051789Methylmercaptan sodium

Product 1

HCID 598456935-Chloro-2-(methylthio)benzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(Step 1) A 3 M aqueous solution of methyl mercaptan sodium salt (15 ml) was added to a solution of 5-chloro-2-fluorobenzonitrile (5.0 g) in DMSO (100 ml). The resulting mixture was stirred at room temperature for 2 hr. To the reaction mixture was added water (200 ml) and the resulting mixture was stirred at room temperature for 30 min. The precipitate was collected by filtration, washed with water, and dried to give 5-chloro-2-(methylsulfanyl)benzonitrile (4.6 g) as a white solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 30 min
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-1d32bcf9e08b4ff5b5f60ca0065d1158
Source dataset
uspto-grants-2011_07
Patent number
US07982044B2

Reaction notes

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