2,3-Dichloro-6-nitroaniline → 2-Chloro-3-phenylthio-6-nitroaniline

HRID 1074850

Reaction equation

HRID 1074850 reaction equation
[Cl:1][C:2]1[C:8](Cl)=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH2:4].[C:13]1([S-:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Na+]>C(#N)C>[Cl:1][C:2]1[C:8]([S:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH2:4]

Participants

4

Reactant 2

HCID 30175542,3-Dichloro-6-nitroanilineHCID 4110039Sodium benzenethiolate

Product 1

HCID 204396382-Chloro-3-phenylthio-6-nitroaniline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 103.5 gm of 2,3-dichloro-6-nitroaniline (0.5 mol) and 72.5 gm of sodium thiophenolate (0.55 mol) was dissolved in 800 ml of acetonitrile, and the solution was refluxed for 5 hours. The mixture was then processed according to the procedure set forth in Example 22 (b)(i). The yield was 108 gm of ochre-coloured, crystalline product (77% of theory), m.p. 144°-146° C.

Workup

  1. temperaturethe solution was refluxed for 5 hours

Sources & evidence

ORD record
ord-18a21a8f09584754a19766f04cae9027
Source dataset
uspto-grants-1983_07
Patent number
US04394159

Linked notes

Loading…