Hydrochloric Acid → 2,5-Dichlorobenzenethiol

HRID 2073639Notes

Reaction equation

HRID 2073639 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1N.Cl.N([O-])=O.[Na+].[Cl-].ClC1C=CC(Cl)=CC=1[N+]#N.NC(N)=[S:28].[OH-].[Na+]>O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[SH:28]

Participants

9

Reactant 6

HCID 313Hydrochloric Acid2×HCID 72622,5-DichloroanilineHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 11805943Benzenediazonium, 2,5-dichloro-, chlorideHCID 23668193Sodium Nitrite

Product 1

HCID 799652,5-Dichlorobenzenethiol

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent3×

Procedure

162 g of 2,5-dichloroaniline are introduced into a mixture of 500 ml of water and 350 ml of 10 N hydrochloric acid and diazotized in the conventional manner at 0° to 5° C. with a solution of 76 g of sodium nitrite in 150 ml of water. The resulting solution of 2,5-dichlorophenyl-diazonium chloride is then run at a temperature of 10° to 15° C. into a well stirred mixture of 91.2 g of thiourea, 5 g of copper(II) sulphate pentahydrate and 5 g of Corlite® in 500 ml of water. The mixture is stirred for approximately 1 further hour, the pH value is raised to 8.5 by means of 330 ml of 10 N sodium hydroxide solution and the mixture is hydrolysed for 1 hour at 90° C. The pH value is then adjusted to 3 by means of 10 N hydrochloric acid and the resulting 2,5-dichlorothiophenol is isolated by steam distillation. (Corlite® is a registered trademark of Corneco-Chemie GmbH., Dortmund) Yield: 154 g of 2,5-dichlorothiophenol (86% of theory), Boiling point: 126° to 129° C./10 mbar.

Workup

  1. customis then run at a temperature of 10° to 15° C. into a well
  2. stirringThe mixture is stirred for approximately 1 further hour

Sources & evidence

ORD record
ord-3a600cc9e06844c486cd5e725ee55584
Source dataset
uspto-grants-1990_04
Patent number
US04918221

Reaction notes

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