4-Bromoaniline → HCID 178509171, compound

HRID 254957Notes

Reaction equation

HRID 254957 reaction equation
BrC1C=CC(N[N:9]=[C:10]([C:13]#[N:14])[C:11]#[N:12])=CC=1.[Br:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.C(#N)CC#N.O.[NH2:29][NH2:30]>>[Br:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][N:9]=[C:10]2[C:11]([NH2:12])=[N:30][N:29]=[C:13]2[NH2:14])=[CH:18][CH:17]=1

Participants

5

Reactant 4

HCID 78074-BromoanilineHCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)2×HCID 23273954(4-Bromophenyl)carbonohydrazonoyl dicyanide

Product 1

HCID 178509171HCID 178509171, compound

Procedure

4-[(4-bromophenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 125 mg (0.5 mmol) of 2-[(4-bromophenyl)hydrazono]malononitrile, which was derived from 4-bromoaniline (172 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 109 mg (78%) of the compound as a yellow solid; 1HNMR (ppm, DMSO-d6): 6.15 (brs, 4H), 7.52 (d, 2H), 7.61 (d, 2H), 10.71 (s, 1H).

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-d6aafa84ac5246e9b3639bc8657cf955
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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