2-Chloro-5-nitroaniline → 1-Chloro-2-isothiocyanato-4-nitrobenzene

HRID 1759390Notes

Reaction equation

HRID 1759390 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH2:11].[CH2:12]=[S:13]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]=[C:12]=[S:13]

Participants

4

Reactant 2

HCID 226912-Chloro-5-nitroanilineHCID 79115Thioformaldehyde

Product 1

HCID 926811-Chloro-2-isothiocyanato-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 50 parts of 2-chloro-5-nitrobenzenamine, 33.4 parts of methanethial and 450 parts of 1,4-dioxane is stirred and refluxed for 4 hours. The reaction mixture is evaporated, yielding 62.2 parts of 1-chloro-2-isothiocyanato-4-nitrobenzene as a residue.

Workup

  1. temperaturerefluxed for 4 hours
  2. customThe reaction mixture is evaporated

Sources & evidence

ORD record
ord-5f4745cba6b3444c926ac0092442e845
Source dataset
uspto-grants-1982_07
Patent number
US04340738

Reaction notes

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