Malononitrile → HCID 178476879, compound

HRID 2095154Notes

Reaction equation

HRID 2095154 reaction equation
C(OP(CC1C=CC(N[N:17]=[C:18]([C:21]#[N:22])[C:19]#[N:20])=CC=1)(=O)OCC)C.[NH2:23][C:24]1[CH:38]=[CH:37][C:27]([CH2:28][P:29](=[O:36])([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32])=[CH:26][CH:25]=1.C(#N)CC#N.O.[NH2:45][NH2:46]>>[CH2:34]([O:33][P:29]([CH2:28][C:27]1[CH:26]=[CH:25][C:24]([NH:23][N:17]=[C:18]2[C:19]([NH2:20])=[N:46][N:45]=[C:21]2[NH2:22])=[CH:38][CH:37]=1)(=[O:36])[O:30][CH2:31][CH3:32])[CH3:35]

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)HCID 88358Diethyl p-aminobenzylphosphonateHCID 86587498HCID 86587498, compound

Product 1

HCID 178476879HCID 178476879, compound

Procedure

{4-[N′-(3,5-Diaminopyrazol-4-ylidene)hydrazino]benzyl}phosphonic acid diethyl ester was prepared using [4-(N′-dicyanomethylenehydrazino)benzyl]phosphonic acid diethyl ester (0.16 g, 0.5 mmol) which was derived from diethyl 4-aminobenzylphosphonate (0.243 g, 1.0 mmol) and malononitrile (1.5 mmol) in a manner similar to that described in Example 2, and hydrazine hydrate. The title compound was purified by flash chromatography and isolated as a golden solid (0.116 g, 66%); 1H NMR (ppm, 200 MHz, DMSO-d6) δ 1.20 (t, 6H), 3.23 (d, 2H), 3.95 (q, 4H), 6.0 (brs, 4H), 7.28 (d, 2H), 7.60 (d, 2H), 10.70.

Workup

  1. customThe title compound was purified by flash chromatography

Sources & evidence

ORD record
ord-7c178b710bbb4669ad00ed05b9a30b3d
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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