3,4-Dichloroaniline → HCID 178509185, compound

HRID 2095131Notes

Reaction equation

HRID 2095131 reaction equation
ClC1C=C(N[N:10]=[C:11]([C:14]#[N:15])[C:12]#[N:13])C=CC=1Cl.[Cl:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[Cl:24])[NH2:20].C(#N)CC#N.O.[NH2:31][NH2:32]>>[Cl:16][C:17]1[CH:18]=[C:19]([NH:20][N:10]=[C:11]2[C:12]([NH2:13])=[N:32][N:31]=[C:14]2[NH2:15])[CH:21]=[CH:22][C:23]=1[Cl:24]

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, compound

Procedure

4-[(3,4-dichlorophenyl)hydrazono]-4H-pyrazole-3,5-diamine 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), 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 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. customPrecipitate formed in the reaction tube
  2. customThe resulting solid was isolated by filtration
  3. customprecipitated from an ethyl acetate solution by the addition of hexanes
  4. customdried

Sources & evidence

ORD record
ord-b319d215f45b49de9bc5e7e51c6c06fe
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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