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

HRID 330705Notes

Reaction equation

HRID 330705 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.CN(C)C(N(C)C)=N.II.ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[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

6

Reactant 4

HCID 807IodineHCID 664601,1,3,3-TetramethylguanidineHCID 70297m-Chloroperbenzoic acidHCID 79304Diphenylmethylidenehydrazine

Product 1

HCID 612301,1'-(Diazomethylene)bis(benzene)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In 500 ml of dichloromethane were dissolved 58.8 g of benzophenone hydrazone, 42 ml of 1,1,3,3-tetramethylguanidine and 150 mg of iodine, and after the mixed solution was cooled to 0° C. to -5° C., 74 g of m-chloroperbenzoic acid (with a purity of 70%) was added, followed by stirring at 0° C. for 40 minutes. The reaction solution was washed with water and dried over sodium sulfate, and the solvent was distilled off to give diphenyldiazomethane.

Workup

  1. temperatureafter the mixed solution was cooled to 0° C. to -5° C.
  2. washThe reaction solution was washed with water
  3. dry with materialdried over sodium sulfate
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-d958c7a94ed64e9d90281d3b95548a09
Source dataset
uspto-grants-1990_01
Patent number
US04897489

Reaction notes

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