Malononitrile → HCID 178509166, compound

HRID 2304433Notes

Reaction equation

HRID 2304433 reaction equation
O1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][N:11]=[C:12]([C:15]#[N:16])[C:13]#[N:14])=[CH:9][C:4]=2[O:3][CH2:2]1.C1OC2C=CC(N)=CC=2O1.C(#N)CC#N.[OH2:32].[NH2:33][NH2:34]>CC(C)=O>[NH2:14][C:13]1[C:12](=[N:11][NH:10][C:8]2[CH:7]=[CH:6][C:5]3[O:32][CH2:2][O:3][C:4]=3[CH:9]=2)[C:15]([NH2:16])=[N:34][N:33]=1

Participants

6

Reactant 4

HCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)2×HCID 843101,3-Benzodioxol-5-amineHCID 722904HCID 722904, compound

Product 1

HCID 178509166HCID 178509166, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

This compound was prepared using 107 mg (0.5 mmol) of 2-(benzo[1,3]dioxol-5-yl-hydrazono)malononitrile, which was derived from 3,4-methylenedioxyaniline (137 mg, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 8, and hydrazine hydrate. Precipitate formed in the reaction tube approximately 10 min after the addition of hydrazine hydrate. The resulting black solid was isolated by filtration, dissolved in acetone, and hexanes was added to precipitate a small amount of black solid. The solid was removed by filtration and the filtrate was concentrated to yield 1.0 mg (1% yield) of the title compound as a black solid. 1H NMR (200 MHz, d6 DMSO) δ: 6.0 (brs, 6H), 6.92 (d, 1H), 7.18 (d, 1H), 7.38 (s, 1H), 10.60 (brs, 1H).

Workup

  1. customThis compound was prepared
  2. customPrecipitate formed in the reaction tube approximately 10 min
  3. customThe resulting black solid was isolated by filtration
  4. customto precipitate a small amount of black solid
  5. customThe solid was removed by filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-82e4a70b96ec4cbbb3064e46ad9baeda
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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