Carbonyl cyanide chlorophenylhydrazone → HCID 178509181, compound

HRID 2304418Notes

Reaction equation

HRID 2304418 reaction equation
[Cl: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.ClC1C=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]([Cl:1])[CH:3]=2)[C:11]([NH2:12])=[N:30][N:29]=1

Participants

5

Reactant 4

HCID 2603Carbonyl cyanide chlorophenylhydrazoneHCID 79323-ChloroanilineHCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)2×

Product 1

HCID 178509181HCID 178509181, compoundYield 14%

Procedure

This compound was prepared using 102 mg (0.5 mmol) of 2-[(3-chlorophenyl)-hydrazono]malononitrile, which was derived from 3-chloroaniline (106 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, precipitated from an ethyl acetate solution by the addition of hexanes, and dried to yield 17 mg (14%) of the title compound as a yellow solid. 1H NMR (ppm, DMSO-d6): 5.98 (br, s, 2H), 6.38 (br, s, 2H), 7.18 (d, 1H), 7.40 (t, 1H), 7.60 (d, 1H), 7.69 (s, 1H), 10.78 (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. customprecipitated from an ethyl acetate solution by the addition of hexanes
  5. customdried

Sources & evidence

ORD record
ord-eeaf9cfbef2540cab4a45fb95a52085a
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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