Water → 2-[(4-Chlorophenyl)sulfanyl]-5-nitrobenzonitrile

HRID 1155742Notes

Reaction equation

HRID 1155742 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-].[Na+].Cl[C:12]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:13]=1[C:14]#[N:15].O>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:12]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:13]=2[C:14]#[N:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7815p-ChlorothiophenolHCID 14798Sodium Hydroxide2×HCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 7067632-[(4-Chlorophenyl)sulfanyl]-5-nitrobenzonitrileYield 99.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 15.2 g (0.105 moles) of 4-chlorothiophenol dissolved in 150 ml of DMSO was added 4.2 g (0.105 moles) of NaOH. The mixture was heated to 60° C. and 18.3 g (0.100 moles) of 2-chloro-5-nitrobenzonitrile was added and the mixture heated at 60° C. for 21/2 hrs. The mixture was cooled and poured into a solution of 100 ml of 2 N aqueous NaOH and 600 ml of water. The product was collected by filtration, washed well with water and dried to obtain 28.8 g of product (99% yield). Recrystallization from ethanol afforded purified 2-((4-chlorophenyl)thio)-5-nitrobenzonitrile, mp 162°-164.5° C.

Workup

  1. temperaturethe mixture heated at 60° C. for 21/2 hrs
  2. temperatureThe mixture was cooled
  3. filtrationThe product was collected by filtration
  4. washwashed well with water
  5. customdried

Sources & evidence

ORD record
ord-dbbe1cf615974ec980927cd7d49922ab
Source dataset
uspto-grants-1982_06
Patent number
US04332820

Reaction notes

Loading…