N-methylbenzohydrazide → N-methylbenzoselenohydrazide

HRID 420117Notes

Reaction equation

HRID 420117 reaction equation
[CH3:1][N:2]([C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[NH2:3].C1C=CC(P2([Se]P(C3C=CC=CC=3)(=[Se])[Se]2)=[Se:19])=CC=1>C1(C)C=CC=CC=1>[CH3:1][N:2]([C:4](=[Se:19])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[NH2:3]

Participants

4

Reactant 2

HCID 242395N-methylbenzohydrazideHCID 50660752,4-Diphenyl-1,3,2,4-diselenadiphosphetane 2,4-diselenide

Product 1

HCID 57551066N-methylbenzoselenohydrazideYield 194.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-methylbenzohydrazide (450 mg, 3.0 mmol) and the Woollins' Reagent (540 mg, 1 mmol) in anhydrous toluene (10 ml), was heated at 120° C. for Ih. The resulting orange solution was cooled to room temperature, the solvent was removed in vacuo and the selenoamide purified by column chromatography on silica gel (3:1 Hexane:EtOAc) and to give N-methylbenzoselenohydrazide (415 mg) in 65% yield.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe selenoamide purified by column chromatography on silica gel (3:1 Hexane:EtOAc)

Sources & evidence

ORD record
ord-9dccb36e76e740d6baae2c152a49a0c9
Source dataset
uspto-grants-2012_01
Patent number
US08093425B2

Reaction notes

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