Malononitrile → HCID 178509166, compound

HRID 2095129Notes

Reaction equation

HRID 2095129 reaction equation
O1C2C=CC(N[N:11]=[C:12]([C:15]#[N:16])[C:13]#[N:14])=CC=2OC1.[CH2:17]1[O:26][C:25]2[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][C:19]=2[O:18]1.C(#N)CC#N.O.[NH2:33][NH2:34]>CC(C)=O>[O:26]1[C:25]2[CH:24]=[CH:23][C:21]([NH:22][N:11]=[C:12]3[C:13]([NH2:14])=[N:34][N:33]=[C:15]3[NH2:16])=[CH:20][C:19]=2[O:18][CH2:17]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, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-(benzo[1,3]dioxol-5-ylhydrazono)-4H-pyrazole-3,5-diamine 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), and hydrazine hydrate. Precipitate formed in the reaction tube approximately 10 minutes 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 compound as a black solid; 1H NMR (200 MHz, DMSO-d6) δ: 6.0 (br s, 6H), 6.92 (d, 1H), 7.18 (d, 1H), 7.38 (s, 1H), 10.60 (br s, 1H).

Workup

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

Sources & evidence

ORD record
ord-e3412e0c02dc48e18dc7519550541106
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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