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

HRID 2082941Notes

Reaction equation

HRID 2082941 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.C(=O)(O)O.NC(N)=N.C(OO)(=O)C>CN(C)C=O.O>[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

7

Reactant 4

HCID 807IodineHCID 6585Peracetic AcidHCID 79304DiphenylmethylidenehydrazineHCID 286947Carbonic acid-guanidine (1:1)

Product 1

HCID 612301,1'-(Diazomethylene)bis(benzene)Yield 60.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To benzophenone hydrazone (19.6 g, 0.1 mole) contained in dimethylformamide (100 ml) together with iodine (4 ml, 1% w/v dichloromethane solution) and guanidine carbonate (75.8 g) was added peracetic acid solution (22.8 ml, 1.27 × 0.1 moles) over 60 minutes followed by a stir time of 60 minutes. The reaction mixture was poured into water (1.5 l) and washed in counter-current batch fashion with dichloromethane (200 ml and 3 × 50 ml) and water (3 × 250 ml). A UV assay at 525 nm on a suitably diluted aliquot corresponded to a yield of 60.5%.

Workup

  1. customfollowed by a stir time of 60 minutes
  2. washwashed in counter-current batch fashion with dichloromethane (200 ml and 3 × 50 ml) and water (3 × 250 ml)
  3. additionA UV assay at 525 nm on a suitably diluted aliquot

Sources & evidence

ORD record
ord-82440e1039bb4e9cbb5fd986d800a409
Source dataset
uspto-grants-1978_04
Patent number
US04083837

Reaction notes

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