Diphosgene → Di(succinimido) carbonate

HRID 1759502Notes

Reaction equation

HRID 1759502 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].Cl[C:10]([O:12]C(Cl)(Cl)Cl)=[O:11]>>[CH2:5]1[C:6](=[O:7])[N:2]([O:1][C:10]([O:12][N:2]2[C:6](=[O:7])[CH2:5][CH2:4][C:3]2=[O:8])=[O:11])[C:3](=[O:8])[CH2:4]1

Participants

3

Reactant 2

HCID 10426DiphosgeneHCID 80170N-Hydroxysuccinimide

Product 1

HCID 676246Di(succinimido) carbonateYield 50.7%

Procedure

11.5 g (0.1 mol) of N-hydroxysuccinimide was admixed with 6 ml (0.05 mol) of trichloromethyl chloroformate (TCF), and the resultant admixture was melted by heating. The heating was continued for 10 minutes and then the resultant melt was allowed to cool and to deposit a colorless crystalline material. This crystalline material was filtered off from the liquid phase and recrystallized from acetonitrile, affording 6.5 g of the titled compound in the form of colorless crystals. Yield 50%.

Workup

  1. temperatureby heating
  2. temperatureto cool
  3. filtrationThis crystalline material was filtered off from the liquid phase
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-b5ba2d3220974111a88b8a072b5d886c
Source dataset
uspto-grants-1982_07
Patent number
US04341707

Reaction notes

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