Trichloroacetyl chloride → 2'-Anilino-2,2-dichloroacetanilide

HRID 866311Notes

Reaction equation

[Cl:1][CH:2]([Cl:6])[C:3](Cl)=[O:4].[C:7]1([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH2:20])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.ClC(Cl)(Cl)C(Cl)=O.C1C=CC(NC2C=CC(N)=CC=2)=CC=1>>[NH:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:3](=[O:4])[CH:2]([Cl:6])[Cl:1])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Reactant 4

HCID 6420Trichloroacetyl chloride

HCID 6593Dichloroacetyl chloride

HCID 7564N-Phenyl-p-phenylenediamine

HCID 68297N-Phenyl-o-phenylenediamine

Product 1

HCID 203203112'-Anilino-2,2-dichloroacetanilide

Procedure

This compound is prepared in the same manner as Compound I, except that dichloroacetyl chloride (5.75 g) and N-phenyl-o-phenylenediamine (7.0 g) are used in place of trichloroacetyl chloride and 4-aminodiphenylamine, respectively. The product is recrystallized from a hexane/benzene (5/1) solvent mixture. The m.p. and chemical analysis are reported in Table I. This compound, which is also called ortho-dichloroacetylaminodiphenylamine, is referred to in U.S. Pat. No. 3,250,774, May 10, 1966, Schmidt et al.

Workup

customThis compound is prepared in the same manner as Compound I
customThe product is recrystallized from a hexane/benzene (5/1) solvent mixture

Sources & evidence

ORD record: ord-d06b27dd79fa4f41a36025800fd17116
Source dataset: uspto-grants-1978_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04098760

Reaction notes

Loading…