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

HRID 2392848Notes

Reaction equation

HRID 2392848 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.II.ClC1C=C(C=CC=1)C(OO)=O>C(Cl)Cl.CN(C)C(N(C)C)=N>[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 3

HCID 807IodineHCID 70297m-Chloroperbenzoic acidHCID 79304Diphenylmethylidenehydrazine

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 664601,1,3,3-TetramethylguanidineSolvent

Procedure

To a solution of benzophenone hydrazone (10 g) in CH2Cl2 (51 mL) is added a 1% w/v solution of iodine in CH2Cl2 (2.05 mL) and 1,1,3,3-tetramethylguanidine (6.43 g). 3-Chloroperoxybenzoic acid (9.7 g) is then added in small portions at room temperature. The solvent is removed in vacuo to provide diphenyl diazomethane. A solution of diphenyl diazomethane (8.78 g) in EtOAc (19 mL) is then added to a cooled (5° C.) solution of Compound 3 in THF (150 mL) and EtOAc (150 mL). The mixture is stirred until completion whereupon it is evaporated to dryness in vacuo. THF (64 mL) is added and the insolubles are filtered off. The filtrate is evaporated in vacuo until crystals begin to form. EtOAc (64 mL) is then added and the mixture is stirred for 1.5 hours at 0°-5° C. The resulting solid is filtered to provide Compound 4.

Workup

  1. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-c0068fca8c2c4f9986667024bd1ee076
Source dataset
uspto-grants-1998_09
Patent number
US05801242

Reaction notes

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