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

HRID 542288Notes

Reaction equation

HRID 542288 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>C(Cl)Cl>[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 CH2Cl2 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 dehydrated 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. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-89e6cb6b462245bc90716021feb82dbb
Source dataset
uspto-grants-1987_04
Patent number
US04656288

Reaction notes

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