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

HRID 1892546Notes

Reaction equation

HRID 1892546 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.CN1CCCC1=O.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 chlorideHCID 1620012-Chloro-4-trifluoromethylaniline

Product 1

HCID 1410944-Amino-3,5-dichlorobenzotrifluorideYield 95%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
57.5 °C

Procedure

A mixture (301 g) of 2-chloro-4-trifluoromethylaniline, 2-chloro-5-trifluoromethylaniline and N-methylpyrrolidone (NMP) (1.06 m/m) was mixed with 500 ml chlorobenzene. Sulfuryl chloride (148.4 g) was added to the mixture at 55-60° C. over a period of 4 hours and the reaction mixture was maintained at 55-60° C. for 4 hours. Reaction medium on treatment and fractionation gave 0.84 m of 2,6-dichloro-4-trifluoromethylaniline, 95% yield on 2-chloro-4-trifluoromethyl aniline.

Workup

  1. customReaction medium on treatment and fractionation

Sources & evidence

ORD record
ord-c30c6b3095a849d4b75e24aa4d63cbdd
Source dataset
uspto-grants-2013_08
Patent number
US08507693B2

Reaction notes

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