Carbonyl cyanide chlorophenylhydrazone → HCID 178509181, compound

HRID 2095115Notes

Reaction equation

HRID 2095115 reaction equation
ClC1C=C(N[N:9]=[C:10]([C:13]#[N:14])[C:11]#[N:12])C=CC=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].C(#N)CC#N.O.[NH2:29][NH2:30]>>[Cl:15][C:16]1[CH:17]=[C:18]([NH:19][N:9]=[C:10]2[C:11]([NH2:12])=[N:30][N:29]=[C:13]2[NH2:14])[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 4

HCID 2603Carbonyl cyanide chlorophenylhydrazoneHCID 79323-ChloroanilineHCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)2×

Product 1

HCID 178509181HCID 178509181, compound

Procedure

4-[(3-chlorophenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 102 mg (0.5 mmol) of 2-[(3-chlorophenyl)hydrazono]malononitrile, which was derived from 3-chloroaniline (106 μL, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 2, and hydrazine hydrate. Precipitate formed in the reaction tube approximately 5 min 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 17 mg (14%) of the compound as a yellow solid; 1H NMR (ppm, DMSO-d6): 5.98 (br, s, 2H), 6.38 (br, s, 2H), 7.18 (d, 1H), 7.40 (t, 1H), 7.60 (d, 1H), 7.69 (s, 1H), 10.78 (s, 1H).

Workup

  1. customPrecipitate formed in the reaction tube approximately 5 min
  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-3164d0dbe0ca429981a411bddf1bc52e
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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