Malononitrile → HCID 178509192, compound

HRID 254958Notes

Reaction equation

HRID 254958 reaction equation
O(C1C=CC(N[N:15]=[C:16]([C:19]#[N:20])[C:17]#[N:18])=CC=1)C1C=CC=CC=1.[O:21]([C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(#N)CC#N.O.[NH2:41][NH2:42]>>[O:21]([C:28]1[CH:29]=[CH:30][C:31]([NH:32][N:15]=[C:16]2[C:17]([NH2:18])=[N:42][N:41]=[C:19]2[NH2:20])=[CH:33][CH:34]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 8764(4-Aminophenoxy)benzeneHCID 24654Hydrazine hydrate (1:1)2×HCID 21955048HCID 21955048, compound

Product 1

HCID 178509192HCID 178509192, compound

Procedure

4-[(4-phenoxyphenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 131 mg (0.5 mmol) of 2-[(4-phenoxyphenyl)hydrazono]malononitrile, which was derived from 4-phenoxyaniline (185 mg, 1.0 mmol) and malononitrile (1.5 mmol), and hydrazine hydrate. The hydrazine hydrate was added to the solution at a temperature of 75° C. despite the fact that the starting material had not fully dissolved. The solution cleared briefly and then a precipitate formed. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 90 mg (61%) of the compound as an orange solid.

Workup

  1. dissolutionhad not fully dissolved
  2. customa precipitate formed
  3. customThe resulting solid was isolated by filtration
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-c1e124963d5a4077b06f163e3447b80e
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

Loading…