Acetic Acid → HCID 20501032, compound

HRID 851774Notes

Reaction equation

HRID 851774 reaction equation
C(OC([N:11]1[C:15]2([C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=3)[C:16]2=[O:33])[C:14](=[O:34])[N:13]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:12]1=[O:40])=O)C1C=CC=CC=1.C(O)(=O)C.C(O)C>[Pd].COCCOC>[CH2:38]([O:37][C:35]([N:13]1[C:14](=[O:34])[C:15]2([C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=3)[C:16]2=[O:33])[NH:11][C:12]1=[O:40])=[O:36])[CH3:39]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 20501034HCID 20501034, compound

Product 1

HCID 20501032HCID 20501032, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3-benzyloxycarbonyl-1-ethoxycarbonyl-1'-(3,4-dichlorobenzyl)spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (1.7 g.), 10% w/w palladium on carbon (0.1 g.), acetic acid (0.3 ml.), ethanol (25 ml.) and 1,2-dimethoxyethane (50 ml.) was hydrogenated at atmospheric pressure for 2 hours. The mixture was separated by filtration through diatomaceous earth and the filtrate was evaporated. The residual oil solidified on treatment with a few drops of toluene. The solid obtained was recrystallised from ethyl acetate/petrol 60-80 to give 1-ethoxycarbonyl-1'-(3,4-dichlorobenzyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (0.7 g.), 176°-179° C.

Workup

  1. customThe mixture was separated by filtration through diatomaceous earth
  2. customthe filtrate was evaporated
  3. customThe solid obtained
  4. customwas recrystallised from ethyl acetate/petrol 60-80

Sources & evidence

ORD record
ord-e78ea9999250417d8e264623f95e726f
Source dataset
uspto-grants-1983_05
Patent number
US04386100

Reaction notes

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