3-(2,6-Dichloro-4-trifluoromethylphenylhydrazino)propionitrile → HCID 21982150, compound

HRID 1838664Notes

Reaction equation

HRID 1838664 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][N:14]=[CH:15][CH2:16][C:17]#[N:18].[Cl:19][C:20]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([Cl:30])[C:21]=1[NH:31][NH:32][CH2:33][CH2:34][C:35]#[N:36]>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][N:14]=[CH:15][CH2:16][C:17]#[N:18].[Cl:19][C:20]1[CH:25]=[C:24]([C:26]([F:28])([F:27])[F:29])[CH:23]=[C:22]([Cl:30])[C:21]=1[N:31]=[N:32][CH2:33][CH2:34][C:35]#[N:36]

Participants

5

Reactant 2

HCID 110878053-(2,6-Dichloro-4-trifluoromethylphenylhydrazino)propionitrileHCID 695517003-{2-[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazinylidene}propanenitrile

Product 2

HCID 21982150HCID 21982150, compoundHCID 695517003-{2-[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazinylidene}propanenitrile

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
65 °C

Procedure

Preparation of 3-(2,6-dichloro-4-trifluoromethylphenylhydrazono)propionitrile from 3-(2,6-dichloro-4-trifluoromethylphenylhydrazino)propionitrile Cupric chloride (0.673 g, 2.5 equivalents) was added in one portion to a solution of 3-(2,6-dichloro-4-trifluoromethylphenylhydrazino)propionitrile (0.591 g, 2 mmol) in chlorobenzene, and the mixture heated at 65° C. for 50 minutes. The reaction was judged to be complete and was cooled, washed (water), dried (magnesium sulfate), evaporated and separated by chromatography on silica gel to give 3-(2,6-dichloro-4-trifluoromethylphenylhydrazono)propionitrile, NMR 3.37 (d, 2H), 7.03 (t, 1H), 7.5 (s, 2H), 7.75 (s, 1H) (35% yield), and 3-(2,6-dichloro-4-trifluoromethylphenylazo)propionitrile, NMR 3.0 (t, 2H), 4.6 (t, 2H), 7.6 (s, 2H) (60% yield).

Workup

  1. temperaturewas cooled
  2. washwashed (water)
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated
  5. customseparated by chromatography on silica gel

Sources & evidence

ORD record
ord-4a8704bec97b4d14b50be84525106a87
Source dataset
uspto-grants-2004_01
Patent number
US06673956B2

Reaction notes

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