Hydrochloric Acid → HCID 20501029, compound

HRID 851772Notes

Reaction equation

HRID 851772 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[Cl:12][C:13]1[CH:14]=[C:15]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]2([C:29](=[O:30])[NH:28][C:27](=[O:31])[NH:26]2)[C:18]1=[O:32].C(=O)([O-])[O-].[Na+].[Na+].Cl>COCCOC>[CH2:5]([O:4][C:2]([N:26]1[C:19]2([C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:17]([CH2:16][C:15]3[CH:33]=[CH:34][C:35]([Cl:36])=[C:13]([Cl:12])[CH:14]=3)[C:18]2=[O:32])[C:29](=[O:30])[NH:28][C:27]1=[O:31])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 13564624HCID 13564624, compound

Product 1

HCID 20501029HCID 20501029, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of benzyl chloroformate (7.6 g.) in 1,2 dimethoxyethane (50 ml.) was added dropwise to a stirred mixture of 1'-(3,4-dichlorobenzyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (7.4 g.) and sodium carbonate (8 g.) in 1,2 dimethoxyethane (200 ml.). When the addition was completed the mixture was stirred for 72 hours and then evaporated. The residual solid was dissolved in warm water (300 ml.) and the solution obtained was carefully acidified (concentrated hydrochloric acid) and then extracted with ethyl acetate (3×150 ml.). The combined extracts were washed successively with water (2×200 ml.) and brine (1×200 ml.) and then dried (MgSO4). Evaporation of the solvent gave a buff solid which was recrystallised from ethyl acetate/petrol 60-80 to give 3-benzyloxycarbonyl-1'-(3,4-dichlorobenzyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (6.5 g.), m.p. 215°-217° C.

Workup

  1. additionWhen the addition
  2. customevaporated
  3. dissolutionThe residual solid was dissolved in warm water (300 ml.)
  4. customthe solution obtained
  5. extractionextracted with ethyl acetate (3×150 ml.)
  6. washThe combined extracts were washed successively with water (2×200 ml.) and brine (1×200 ml.)
  7. dry with materialdried (MgSO4)
  8. customEvaporation of the solvent
  9. customgave a buff solid which
  10. customwas recrystallised from ethyl acetate/petrol 60-80

Sources & evidence

ORD record
ord-12a53cf6ab2a417ea692ecafe2b30e8a
Source dataset
uspto-grants-1983_05
Patent number
US04386100

Reaction notes

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