Malononitrile → HCID 178509166, compound

HRID 254963Notes

Reaction equation

HRID 254963 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-68a60e9414a747e5a930fe38eb975883
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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