1,1'-(Diazomethylene)bis(benzene) → HCID 14010095, compound

HRID 1788786Notes

Reaction equation

HRID 1788786 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[O:12][C:13](=[CH2:17])[C:14]([OH:16])=[O:15].[C:18]1([C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N+]=[N-])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[O:12][C:13](=[CH2:17])[C:14]([O:16][CH:24]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:15]

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 19752204HCID 19752204, compound

Product 1

HCID 14010095HCID 14010095, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[(1,3-Dioxo-2H-isoindol-2-yl)oxy]-2-propenoic acid (39.6 g, 0.17 mole) was dissolved in 800 ml of acetonitrile and a solution of diphenyldiazomethane (43.4 g, 0.224 mole/1000 ml acetonitrile) was added dropwise over 3 hours at 0° C. The reaction solution was evaporated to a solid which was triturated with hexane. The resulting solid was dissolved in dichloromethane and filtered through a pad of silica gel (Kieselgel 60). Addition of hexane produced 47.7 g of the title compound.

Workup

  1. customThe reaction solution was evaporated to a solid which
  2. customwas triturated with hexane
  3. dissolutionThe resulting solid was dissolved in dichloromethane
  4. filtrationfiltered through a pad of silica gel (Kieselgel 60)
  5. additionAddition of hexane

Sources & evidence

ORD record
ord-62540daf740f4ebdb0f0fb22e0de0d65
Source dataset
uspto-grants-1987_08
Patent number
US04684722

Reaction notes

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