Malononitrile → HCID 178509173, compound

HRID 2304427Notes

Reaction equation

HRID 2304427 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][N:9]=[C:10]([C:13]#[N:14])[C:11]#[N:12])[CH:5]=[CH:6][CH:7]=1.BrC1C=C(C=CC=1)N.C(#N)CC#N.O.[NH2:29][NH2:30]>>[NH2:14][C:13]1[C:10](=[N:9][NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[C:11]([NH2:12])=[N:30][N:29]=1

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 115623-BromoanilineHCID 24654Hydrazine hydrate (1:1)2×HCID 4199189HCID 4199189, compound

Product 1

HCID 178509173HCID 178509173, compoundYield 66%

Procedure

This compound was prepared using 125 mg (0.5 mmol) of 2-[(3-bromophenyl)-hydrazono]malononitrile, which was derived from 3-bromoaniline (172 mg, 1.0 mmol) and malononitrile (1.5 mmol) as. described in Example 8, 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 93 mg (66%) of the title compound as an orange solid. 1H NMR (ppm, DMSO-d6): 6.2 (br s, 4H), 7.21-7.32 (m, 2H), 7.50-7.62 (m, 1H), 7.90 (s, 1H), 10.71 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-da9b3b1aece94cf196be01260d774b22
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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