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

HRID 10766Notes

Reaction equation

HRID 10766 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][NH:14][CH2:15][CH2:16][C:17]#[N:18]>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: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[N:13]=[N:14][CH2:15][CH2:16][C:17]#[N:18]

Participants

4

Reactant 1

HCID 110878053-(2,6-Dichloro-4-trifluoromethylphenylhydrazino)propionitrile

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

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-4trifluoromethylphenylazo)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-51889edae8a3452c876a139b2f003a44
Source dataset
uspto-grants-2006_08
Patent number
US07094906B2

Reaction notes

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