Malononitrile → HCID 178509189, compound

HRID 2304429Notes

Reaction equation

HRID 2304429 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][N:9]=[C:10]([C:13]#[N:14])[C:11]#[N:12])=[CH:4][CH:3]=1.IC1C=CC(N)=CC=1.C(#N)CC#N.O.[NH2:29][NH2:30]>>[NH2:14][C:13]1[C:10](=[N:9][NH:8][C:5]2[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=2)[C:11]([NH2:12])=[N:30][N:29]=1

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 108934-IodoanilineHCID 24654Hydrazine hydrate (1:1)2×HCID 681317HCID 681317, compound

Product 1

HCID 178509189HCID 178509189, compoundYield 70%

Procedure

This compound was prepared using 148 mg (0.5 mmol) of 2-[(4-iodophenyl)hydrazono]-malononitrile, which was derived from 4-iodoaniline (219 mg, 101.0 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 114 mg (70%) of the title compound as a yellow solid.

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-a036253e1fa64bf4b1e54e8e45712636
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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