Hydrochloric Acid → HCID 13691150, compound

HRID 1248331Notes

Reaction equation

HRID 1248331 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2([CH2:15][C:14](=[O:16])[NH:13][C:12]2=[O:17])[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=O)C.O>[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([CH2:15][C:14](=[O:16])[NH:13][C:12]2=[O:17])[C:4]1=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 76093,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 20236136HCID 20236136, compound

Product 1

HCID 13691150HCID 13691150, compoundYield 16.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Sodium hydride (1.1 g.; 23 mM; 50% w/w oil dispersion) was added to a stirred solution of spiro[pyrrolidine-3,3'-indoline]-2,2',5-trione (2.1 g.; 9.7 mM) in DMF (40 ml.), under an atmosphere of nitrogen. The mixture was stirred until effervescence had ceased and then heated to approximately 90° C. 3,4-Dichlorobenzyl chloride (2.2 g., 11.2 mM) was added dropwise. The reaction mixture was then allowed to cool to ambient temperature, stirred for 16 hours, and poured into water. The aqueous mixture was acidified (concentrated hydrochloric acid) and extracted with ethyl acetate (2×150 ml.). The combined extracts were washed with water (3×150 ml.), brine (150 ml.), dried MgSO4) and evaporated. The residual oil was purified by chromatography on silica gel (150 g.) using an increasing gradient of ethyl acetate in toluene as eluant. Fractions were monitored by TLC (SiO2 : 50% v/v EtOAc/toluene) and those containing the major component (relative flow value: 0.5) were evaporated to give 1'-(3,4-dichlorobenzyl)-spiro[pyrrolidine-3,3'-indoline]-2,2',5-trione (0.6 g.), m.p. 205°-207° C. (recrystallised twice from MeOH).

Workup

  1. temperatureto cool to ambient temperature
  2. stirringstirred for 16 hours
  3. extractionextracted with ethyl acetate (2×150 ml.)
  4. washThe combined extracts were washed with water (3×150 ml.), brine (150 ml.), dried MgSO4) and
  5. customevaporated
  6. customThe residual oil was purified by chromatography on silica gel (150 g.)
  7. customthose containing the major component (relative flow value: 0.5) were evaporated

Sources & evidence

ORD record
ord-1d3c1774db294fe3accc3b98a0d62956
Source dataset
uspto-grants-1985_06
Patent number
US04523021

Reaction notes

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