Hydrochloric Acid → HCID 20501037, compound

HRID 851771Notes

Reaction equation

HRID 851771 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([C:18](=[O:19])[NH:17][C:16](=[O:20])[NH:15]2)[C:7]1=[O:21].[H-].[Na+].Br[CH:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:31](=[O:32])[O:30]1.Cl>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([C:18](=[O:19])[NH:17][C:16](=[O:20])[N:15]2[CH:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:31](=[O:32])[O:30]2)[C:7]1=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 962181(3H)-Isobenzofuranone, 3-bromo-HCID 13564624HCID 13564624, compound

Product 1

HCID 20501037HCID 20501037, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1'-(3,4-Dichlorobenzyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (1.8 g.) was stirred in anhydrous N,N-dimethylformamide (50 ml.) under an atmosphere of nitrogen at 25° C. Sodium hydride (0.25 g; 50% w/v oil dispersion) was added, and the mixture stirred for 30 minutes. 3-Bromophthalide (1.15 g.) was then added. The mixture was stirred for 16 hours and then poured into water (150 ml.). The mixture was acidified (concentrated hydrochloric acid) and then extracted with ethyl acetate (150 ml.). The extract was washed with water (2×150 ml.), brine (150 ml.) and then dried (MgSO4). The dry solution was evaporated onto silica gel (10 g., Merck type 7734) which was then added to the top of a column of silica gel (150 g., Merck type 7734) made up in toluene. The column was eluted with an increasing concentration of ethyl acetate in toluene up to 25% v/v. The fractions containing the major product [Relative flow value: 0.5 on Merck SiO2TLC plates No. 5715; eluant: EtOAc/toluene, 1:1 v/v] were collected and evaporated to give an oil which crystallised on treatment with ethyl acetate/petrol 60-80 to give 1'-(3,4-dichlorobenzyl)-3-phthalidyl-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (0.4 g.), m.p. 154°-158° C.

Workup

  1. stirringThe mixture was stirred for 16 hours
  2. extractionextracted with ethyl acetate (150 ml.)
  3. washThe extract was washed with water (2×150 ml.), brine (150 ml.)
  4. dry with materialdried (MgSO4)
  5. customThe dry solution was evaporated onto silica gel (10 g., Merck type 7734) which
  6. additionwas then added to the top of a column of silica gel (150 g., Merck type 7734)
  7. washThe column was eluted with an increasing concentration of ethyl acetate in toluene up to 25% v/v
  8. additionThe fractions containing the major product [Relative flow value
  9. customeluant: EtOAc/toluene, 1:1 v/v] were collected
  10. customevaporated
  11. customto give an oil which
  12. customcrystallised on treatment with ethyl acetate/petrol 60-80

Sources & evidence

ORD record
ord-e2711f522cf6422cb8057d85d700d64a
Source dataset
uspto-grants-1983_05
Patent number
US04386100

Reaction notes

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