Diphenylmethylidenehydrazine → 1,1'-(Diazomethylene)bis(benzene)

HRID 2249202Notes

Reaction equation

HRID 2249202 reaction equation
[C:1](=[N:14][NH2:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOCC.O.OO.[Ni]>[C:2]1([C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N+:14]=[N-:15])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 79304Diphenylmethylidenehydrazine

Product 1

HCID 612301,1'-(Diazomethylene)bis(benzene)Yield 100%

Reagents, catalysts & solvents 2

HCID 7131114086676-91-7CatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 0.59 g (3 mmol) of benzophenone hydrazone in 12 ml of ether is added dropwise at room temperature to a suspension of 2.95 g of nickel peroxide hydrate in 12 ml of ether, the mixture is stirred for one hour and the violet solution is filtered with suction through Celite and concentrated. The 3 mmol of diphenyldiazomethane obtained in this way are dissolved in 32 ml of absolute acetone and, while cooling in ice, added dropwise to a solution of 1.31 g (2.5 mmol) of 2-[N-(1S -menthyloxycarbonyl-3-phenylpropyl)-S-alanyl]-(1S,3S,5S)2-azabicyclo[3.3.0]octane-3-carboxylic acid (see Example 45) in 32 ml of absolute acetone. The mixture is then stirred at room temperature for 38 hours and concentrated, and the crude product is purified by column chromatography on silica gel (mobile phase toluene/ethanol 99.5:0.5 and cyclohexane/ethyl acetate 8:2).

Workup

  1. filtrationthe violet solution is filtered with suction through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-04b43f2e84934ca595431588f4648767
Source dataset
uspto-grants-1991_08
Patent number
US05043346

Reaction notes

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