Hydrochloric Acid → HCID 20279335, compound

HRID 1633003Notes

Reaction equation

HRID 1633003 reaction equation
[OH-].[K+].[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].[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1.Cl>CS(C)=O.O>[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:3]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]3([CH2:15][C:14](=[O:16])[NH:13][C:12]3=[O:17])[C:4]2=[O:18])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 685274-Bromobenzyl bromideHCID 20236136HCID 20236136, compound

Product 1

HCID 20279335HCID 20279335, compoundYield 8.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Ethanolic potassium hydroxide (12 ml., 1M) was added to a stirred solution of spiro[pyrrolidine-3,3'-indoline]-2,2',5-trione (1.0 g.) in dimethyl sulphoxide (10 ml.). 4-Bromobenzyl bromide (1.4 g.) was then added to the clear solution which was stirred for 4 hours. This solution was then added to water (100 ml.). The mixture was acidified (concentrated hydrochloric acid). The precipitate was collected, washed with water, air-dried and recrystallised from ethyl acetate/petrol 60-80 to give 1'-(4-bromobenzyl)spiro[pyrrolidine-3,3-indoline]-2,2',5-trione (0.15 g.) m.p. 218°-220° C.

Workup

  1. customThe precipitate was collected
  2. washwashed with water
  3. customair-dried
  4. customrecrystallised from ethyl acetate/petrol 60-80

Sources & evidence

ORD record
ord-c2adf898dadf47be99886b841a224a08
Source dataset
uspto-grants-1984_10
Patent number
US04478847

Reaction notes

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