Sodium Carbonate → HCID 20501034, compound

HRID 851773Notes

Reaction equation

HRID 851773 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH2:7]([O:14][C:15]([N:17]1[C:21]2([C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=3)[C:22]2=[O:39])[C:20](=[O:40])[NH:19][C:18]1=[O:41])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.CCOCC>[CH2:7]([O:14][C:15]([N:17]1[C:21]2([C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=3)[C:22]2=[O:39])[C:20](=[O:40])[N:19]([C:2]([O:4][CH2:5][CH3:6])=[O:3])[C:18]1=[O:41])=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 20501029HCID 20501029, compound

Product 1

HCID 20501034HCID 20501034, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Ethyl chloroformate (0.6 g.) was added slowly to a stirred mixture of 3-benzyloxycarbonyl-1'-(3,4-dichlorobenzyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (2.55 g.) and sodium carbonate (2.0 g.) in 1,2-dimethoxyethane (60 ml.). The mixture was stirred for 16 hours and the solid then removed by filtration. The filtrate was evaporated to give an oil which solidified on treatment with a few drops of ether. This solid was recrystallised from ethyl acetate/petrol 60-80 to give 3-benzyloxycarbonyl-1-ethoxycarbonyl-1'(3,4-dichlorobenzyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (1.8 g.), m.p. 128°-131° C.

Workup

  1. customthe solid then removed by filtration
  2. customThe filtrate was evaporated
  3. customto give an oil which
  4. customThis solid was recrystallised from ethyl acetate/petrol 60-80

Sources & evidence

ORD record
ord-10e9e19856174acaab87876070905d9a
Source dataset
uspto-grants-1983_05
Patent number
US04386100

Reaction notes

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