Malononitrile → HCID 178509188, compound

HRID 2304432Notes

Reaction equation

HRID 2304432 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][N:10]=[C:11]([C:14]#[N:15])[C:12]#[N:13])[CH:5]=[CH:6][C:7]=1[F:8].FC1C=C(C=CC=1F)N.C(#N)CC#N.O.[NH2:31][NH2:32]>>[NH2:15][C:14]1[C:11](=[N:10][NH:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)[C:12]([NH2:13])=[N:32][N:31]=1

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)2×HCID 774693,4-DifluoroanilineHCID 21954996HCID 21954996, compound

Product 1

HCID 178509188HCID 178509188, compoundYield 38%

Procedure

This compound was prepared using 103 mg (0.5 mmol) of 2-[(3,4-difluorophenyl)-hydrazono]malononitrile, which was derived from 3,4-difluoroaniline (99 μL, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 8, and hydrazine hydrate. Precipitate formed in the reaction tube approximately 5 min after the addition of hydrazine hydrate. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 45 mg (38%) of the title compound as a yellow solid. 1H NMR (ppm, DMSO-d6): 6.18 (br s, 4H), 7.28-7.55 (m, 2H), 7.70-7.82 (m, 1H), 10.80 (br s, 1H).

Workup

  1. customThis compound was prepared
  2. customPrecipitate formed in the reaction tube approximately 5 min
  3. customThe resulting solid was isolated by filtration
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-a97cc90a2f6e4b9c94e035a1587b2822
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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