Benzenamine, 2-chloro-5-(trifluoromethyl)- → 4-Amino-3,5-dichlorobenzotrifluoride

HRID 1892547Notes

Reaction equation

HRID 1892547 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:13]C1C=CC(C(F)(F)F)=CC=1N.CN1C(=O)CCC1.S(Cl)(Cl)(=O)=O>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=[C:5]([Cl:13])[C:3]=1[NH2:4]

Participants

6

Reactant 4

HCID 8475Benzenamine, 2-chloro-5-(trifluoromethyl)-HCID 13387N-methyl-2-pyrrolidoneHCID 24648Sulfuryl chloride2×HCID 1620012-Chloro-4-trifluoromethylaniline

Product 1

HCID 1410944-Amino-3,5-dichlorobenzotrifluorideYield 94%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture (276 g) of 2-chloro-4-trifluoromethylaniline, 2-chloro-5-trifluoromethylaniline and NMP (0.73 m/m) was mixed with 500 ml chlorobenzene. Sulfuryl chloride (135 g) was added to the mixture at 55-60° C. liquid temperature over a period of 4 hours and the reaction temperature was maintained for further 2 hours. Additional 20.2. g of sulfuryl chloride was added for completion of reaction. Reaction medium on treatment and fractionation gave 2,6-dichloro-4-trifluoromethylaniline, in 94% yield on 2-chloro-4-trifluoromethylaniline.

Workup

  1. temperaturethe reaction temperature was maintained for further 2 hours
  2. customReaction medium on treatment and fractionation

Sources & evidence

ORD record
ord-097983db62f840b3a7242d3be3467ff0
Source dataset
uspto-grants-2013_08
Patent number
US08507693B2

Reaction notes

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