Potassium Carbonate → HCID 13248079, compound

HRID 463699Notes

Reaction equation

HRID 463699 reaction equation
C(=O)([O-])[O-].[K+].[K+].C(O[C:15]([O:17][C:18]1([C:38]([NH2:40])=[O:39])[C:26]2[C:21](=[C:22]([F:27])[CH:23]=[CH:24][CH:25]=2)[N:20]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=2)[C:19]1=[O:37])=[O:16])C1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:36][C:31]1[CH:30]=[C:29]([CH:34]=[CH:33][C:32]=1[Cl:35])[CH2:28][N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])[C:18]2([O:17][C:15](=[O:16])[NH:40][C:38]2=[O:39])[C:19]1=[O:37]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 13248078HCID 13248078, compound

Product 1

HCID 13248079HCID 13248079, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Potassium carbonate (6.0 g.) was added to a solution of 3-benzyloxycarbonyloxy-1-(3,4-dichlorobenzyl)-7-fluoro-2-oxoindoline-3-carboxamide (2.0 g.) in toluene (100 ml.). The mixture was stirred and heated under reflux for 1 hour. The toluene was removed by evaporation and the residue partitioned between ether (100 ml.) and water (100 ml.). The aqueous phase was adjusted to pH 5 with 2M hydrochloric acid. The ether phase was then separated, washed with water, brine and then dried (MgSO4) and evaporated to give 1'-(3,4-dichlorobenzyl)-7'-fluorospiro[oxazolidine-5,3'-indoline]-2,2',4-trione, as a solid, m.p. 140°-142° C. (recrystallised from ethyl acetate/petrol 60-80).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. customThe toluene was removed by evaporation
  4. customthe residue partitioned between ether (100 ml.) and water (100 ml.)
  5. customThe ether phase was then separated
  6. washwashed with water, brine
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-0df872b8fa544a56a49ebb3e8f1e7626
Source dataset
uspto-grants-1985_10
Patent number
US04544662

Reaction notes

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