Carbonyl cyanide chlorophenylhydrazone → HCID 178509181, compound

HRID 254949Notes

Reaction equation

HRID 254949 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-de4c35b6027c4e83b2a8c88928fda26e
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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