Benzenamine, N-(2,2,6,6-tetrachlorocyclohexylidene)- → 2,6-Dichloro-N-phenylaniline

HRID 1165350Notes

Reaction equation

HRID 1165350 reaction equation
[C:1]1([N:7]=[C:8]2[C:13](Cl)([Cl:14])[CH2:12][CH2:11][CH2:10][C:9]2(Cl)[Cl:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>ClC1C=CC=CC=1>[C:1]1([NH:7][C:8]2[C:9]([Cl:16])=[CH:10][CH:11]=[CH:12][C:13]=2[Cl:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 11809088Benzenamine, N-(2,2,6,6-tetrachlorocyclohexylidene)-

Product 1

HCID 848672,6-Dichloro-N-phenylanilineYield 84.9%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
25 °C

Procedure

A 1 l glass reactor was charged with 100 g (0.32 mole) of N-phenyl-2,2,6,6-tetrachlorocyclohexaneimine obtained in Example 1 and 500 g of chlorobenzene, and the mixture was heated in an oil bath with stirring. While keeping the reaction temperature at 100° C., the reaction was continued for 5 hours. After the reaction was completed, the reaction mixture was cooled to 25° C., and washed with 300 g of a 10% aqueous solution of sodium hydroxide. Then, the organic layer was dried with sodium sulfuric anhydride, from which chlorobenzene was distilled away under reduced pressure to give 64.7 g of N-phenyl-2,6-dichloroaniline in the state of a black solid (yield: 85%, mp: 49.5° to 50.7° C.). The obtained N-phenyl-2,6-dichloroaniline had a purity of 92.1% measured by means of gas chromatography.

Workup

  1. temperaturethe mixture was heated in an oil bath
  2. customat 100° C.
  3. washwashed with 300 g of a 10% aqueous solution of sodium hydroxide
  4. dry with materialThen, the organic layer was dried with sodium sulfuric anhydride, from which chlorobenzene
  5. distillationwas distilled away under reduced pressure

Sources & evidence

ORD record
ord-7b14caa1ac3840bdb0cd59ee9e07b191
Source dataset
uspto-grants-1990_03
Patent number
US04908479

Reaction notes

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