Hydrochloric Acid → HCID 20501038, compound

HRID 851769Notes

Reaction equation

HRID 851769 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(=O)([O-])[O-].[Na+].[Na+].Cl>COCCOC>[CH2:5]([O:4][C:2]([N:21]1[C:14]2([C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:12]([CH2:11][C:10]3[CH:28]=[CH:29][C:30]([Cl:31])=[C:8]([Cl:7])[CH:9]=3)[C:13]2=[O:27])[C:24](=[O:25])[NH:23][C:22]1=[O:26])=[O:3])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 13564624HCID 13564624, compound

Product 1

HCID 20501038HCID 20501038, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of ethyl chloroformate (0.55 g.) in 1,2-dimethoxyethane (20 ml.) was added dropwise 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 1,2-dimethoxyethane (60 ml.). When the addition was completed, the mixture was stirred for 16 hours and then evaporated. The residual solid was dissolved in warm water (150 ml.) and the solution obtained was slowly acidified (concentrated hydrochloric acid). The solid which was precipitated was separated by filtration, washed with water, air-dried and recrystallised twice from propan-2-ol/petrol 60-80 to give 3-ethoxycarbonyl-1'-(3,4-dichlorobenzyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (0.35 g.), m.p. 192°-194° C.

Workup

  1. additionWhen the addition
  2. customevaporated
  3. dissolutionThe residual solid was dissolved in warm water (150 ml.)
  4. customthe solution obtained
  5. customThe solid which was precipitated
  6. customwas separated by filtration
  7. washwashed with water
  8. customair-dried
  9. customrecrystallised twice from propan-2-ol/petrol 60-80

Sources & evidence

ORD record
ord-ad9ab16feb954406ad2e8e5af24bbdef
Source dataset
uspto-grants-1983_05
Patent number
US04386100

Reaction notes

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