Malononitrile → HCID 178509184, compound

HRID 2304441Notes

Reaction equation

HRID 2304441 reaction equation
[I: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.IC1C=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]([I:1])[CH:3]=2)[C:11]([NH2:12])=[N:30][N:29]=1

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 122713-IodoanilineHCID 24654Hydrazine hydrate (1:1)2×HCID 21955020HCID 21955020, compound

Product 1

HCID 178509184HCID 178509184, compoundYield 74%

Procedure

This compound was prepared using 148 mg (0.5 mmol) of 2-[(3-iodophenyl)hydrazono]-malononitrile, which was derived from 3-iodoaniline (219 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 122 mg (74%) of the title compound as a mustard coloured 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-e3aeeaaa547b4af78d65bfa52a6e2223
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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