1,2-Dimethoxyethane → HCID 20501025, compound

HRID 851768Notes

Reaction equation

HRID 851768 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[Cl:7][C:8]1[CH:9]=[C:10]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]2([C:24](=[O:25])[NH:23][C:22](=[O:26])[NH:21]2)[C:13]1=[O:27].[C:32](=[O:35])([O-])[O-:33].[Na+].[Na+].[CH2:38]([CH2:41]OC)OC>>[Cl:7][C:8]1[CH:9]=[C:10]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]2([C:24](=[O:25])[N:23]([C:2]([O:4][CH2:5][CH3:6])=[O:3])[C:22](=[O:26])[N:21]2[C:32]([O:33][CH2:38][CH3:41])=[O:35])[C:13]1=[O:27]

Participants

5

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 13564624HCID 13564624, compound

Product 1

HCID 20501025HCID 20501025, compound

Conditions

Temperature
25 °C

Procedure

Ethyl chloroformate (1.1 g.) was added to a stirred mixture of 1'-(3,4-dichlorobenzyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (1.8 g.) and sodium carbonate (2.0 g.) in dimethoxyethane (60 ml.). The mixture was stirred at 25° C. for 16 hours. The solid was removed by filtration and the filtrate was evaporated. The residue obtained was recrystallised twice from ethyl acetate/petrol 60-80 to give 1'-(3,4-dichlorobenzyl)-1,3-di(ethoxycarbonyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (0.6 g.), m.p. 180°-182° C.

Workup

  1. customThe solid was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residue obtained
  4. customwas recrystallised twice from ethyl acetate/petrol 60-80

Sources & evidence

ORD record
ord-69e069854a8f460d91256e866f1a6fff
Source dataset
uspto-grants-1983_05
Patent number
US04386100

Reaction notes

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