(4-Chloroanilino)(2,6-dichlorophenyl)acetonitrile → 2-[(4-chlorophenyl)amino]-2-(2,6-dichlorophenyl)acetamide

HRID 1389931Notes

Reaction equation

HRID 1389931 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:10]#[N:11].S(=O)(=O)(O)[OH:21].O>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=1)[C:10]([NH2:11])=[O:21]

Participants

3

Reactant 2

HCID 3018554(4-Chloroanilino)(2,6-dichlorophenyl)acetonitrileHCID 21910475Sulfuric acid hydrate (1:1)

Product 1

HCID 4864592-[(4-chlorophenyl)amino]-2-(2,6-dichlorophenyl)acetamide

Procedure

50 Parts of 2,6-dichloro-α-[(4-chlorophenyl)amino]benzeneacetonitrile are added portionwise to 270 parts of sulfuric acid/water (10:1 by volume) and the whole is stirred overnight at room temperature. The reaction mixture is poured onto 2000 parts of ice-water. The precipitated product is filtered off, washed on the filter successively with water and 2-propanol and recrystallized from 560 parts of 2-propanol at -20° C., yielding 43.1 parts of 2,6-dichloro-α-[(4-chlorophenyl)amino]benzeneacetamide; mp. 178° C.

Workup

  1. filtrationThe precipitated product is filtered off
  2. washwashed on the
  3. filtrationfilter successively with water and 2-propanol
  4. customrecrystallized from 560 parts of 2-propanol at -20° C.

Sources & evidence

ORD record
ord-66d324c1cc544111a7e96afc5860cb5d
Source dataset
uspto-grants-1981_01
Patent number
US04246429

Reaction notes

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