Hydrochloric Acid → HCID 13564624, compound

HRID 851765Notes

Reaction equation

HRID 851765 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2([C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12]2)[C:4]1=[O:18].[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:23]Cl.Cl>CN(C)C=O.O.O1CCCC1>[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:23][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2([C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12]2)[C:4]1=[O:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 76093,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 15554858HCID 15554858, compound

Product 1

HCID 13564624HCID 13564624, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (1.5 g., 50% w/w dispersion in mineral oil) was added continuously to a solution of spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (2.17 g.) in N,N-dimethylformamide (40 ml.) and water (20 ml.). The resultant mixture was stirred for 30 minutes and then a solution of 3,4-dichlorobenzyl chloride (1.95 g.) in tetrahydrofuran (5 ml.) was added dropwise during 10 minutes. The solution obtained was stirred at room temperature for two hours and then poured into water (150 ml.). The mixture was acidified with concentrated hydrochloric acid and then extracted with ether (2×100 ml.). The combined extracts were washed with water (3×100 ml.), then with saturated sodium chloride solution (100 ml.), dried (MgSO4) and evaporated. The residual solid was dissolved in chloroform and purified by chromatography on silica (25 g.) using an increasing concentration of ethyl acetate in cyclohexane as eluant. Evaporation of the ethyl acetate rich fractions gave 1'-(3,4-dichlorobenzyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione identical with that obtained in Prep. 1.

Workup

  1. customThe solution obtained
  2. extractionextracted with ether (2×100 ml.)
  3. washThe combined extracts were washed with water (3×100 ml.)
  4. dry with materialwith saturated sodium chloride solution (100 ml.), dried (MgSO4)
  5. customevaporated
  6. dissolutionThe residual solid was dissolved in chloroform
  7. custompurified by chromatography on silica (25 g.)
  8. customEvaporation of the ethyl acetate rich fractions

Sources & evidence

ORD record
ord-d40b14bce6e04c868a4ada5d76b74f52
Source dataset
uspto-grants-1983_05
Patent number
US04386100

Reaction notes

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