3,4-Dichloroaniline → HCID 178509185, compound

HRID 2304436Notes

Reaction equation

HRID 2304436 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][N:10]=[C:11]([C:14]#[N:15])[C:12]#[N:13])[CH:5]=[CH:6][C:7]=1[Cl:8].ClC1C=C(C=CC=1Cl)N.C(#N)CC#N.O.[NH2:31][NH2:32]>>[NH2:15][C:14]1[C:11](=[N:10][NH:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[C:12]([NH2:13])=[N:32][N:31]=1

Participants

5

Reactant 4

HCID 72573,4-DichloroanilineHCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)2×HCID 77308Propanedinitrile, ((3,4-dichlorophenyl)hydrazono)-

Product 1

HCID 178509185HCID 178509185, compoundYield 39%

Procedure

This compound was prepared using 120 mg (0.5 mmol) of 2-[(3,4-dichlorophenyl)-hydrazono]malononitrile, which was derived from 3,4-dichloroaniline (162 mg, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 8, and hydrazine hydrate. Precipitate formed in the reaction tube immediately after the addition of hydrazine hydrate. The resulting solid was isolated by filtration, precipitated from an ethyl acetate solution by the addition of hexanes, and dried to yield 53 mg (39%) of the title compound as a yellow solid. 1H NMR (ppm, DMSO-d6): 6.30 (br, s, 4H), 7.55-7.79 (m, 2H), 7.95 (s, 1H), 10.80 (s, 1H).

Workup

  1. customThis compound was prepared
  2. customPrecipitate formed in the reaction tube
  3. customThe resulting solid was isolated by filtration
  4. customprecipitated from an ethyl acetate solution by the addition of hexanes
  5. customdried

Sources & evidence

ORD record
ord-596ffabf9ef443d6a51ca5344b5a92dc
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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