2,5-Dichloronitrobenzene → 2,5-Dichloroaniline

HRID 1579743Notes

Reaction equation

HRID 1579743 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-])=O.S.[Na]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH2:9]

Participants

4

Reactant 2

HCID 69772,5-DichloronitrobenzeneHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 72622,5-Dichloroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

576 Parts of 2,5-dichloro-nitrobenzene and 300 parts of water were placed in a stirring apparatus and reacted in the same manner as described in Example 1 with 1,446 parts of a 36% sodium hydrogen sulfide solution at a temperature within the range of from 80° to 85°C. Then, the 2,5-dichloroaniline formed as by-product was separated by steam distillation. After cooling to 20°C 1,210 parts of sodium sulfite and 430 parts of xylene were successively added and the pH was adjusted at 6 at a temperature within the range of from 8° to 12°C during 3 to 4 hours with 550 parts of 30% hydrochloric acid while stirring. After precipitation and separation of the organic phase, the aqueous phase was stirred once with 174 parts of xylene. 4-Chloro-2-amino-thiophenol was isolated from the organic phase, combined by vacuum distillation.

Workup

  1. customreacted in the same manner

Sources & evidence

ORD record
ord-6fa69c23e5ad44909318ee3626106a75
Source dataset
uspto-grants-1976_01
Patent number
US03931321

Reaction notes

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