Potassium Carbonate → HCID 15453519, compound

HRID 2228651Notes

Reaction equation

HRID 2228651 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.C([C:15]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:16]=1[O:17][CH2:18][CH2:19][N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30])(=O)C.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[F:35][C:32]1[CH:33]=[CH:34][C:15]([OH:9])=[C:16]([CH:31]=1)[O:17][CH2:18][CH2:19][N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 15453517HCID 15453517, compound

Product 1

HCID 15453519HCID 15453519, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 26 g of meta-chloroperbenzoic acid (at 55%, 82.9 mmol) in 220 ml of dichloromethane is stirred for one hour and then transferred into a separating funnel. The aqueous phase is separated out and the organic phase is placed in a round-bottomed flask and cooled to 0° C. 18 9 of 2-[2-(2-acetyl-5-fluoro-phenoxy)ethyl]isoindole-1,3-dione (5) (55 mmol) are added portionwise and the mixture is stirred at room temperature for 16 hours. 6.9 g of sodium bicarbonate (82 mmol) are then introduced portionwise and the mixture is stirred for one hour. The mixture is then concentrated under vacuum and 200 ml of methanol are added, followed by addition of 15.2 g of potassium carbonate (110 mmol). The mixture is stirred for 4 hours at room temperature and the solvent is then evaporated off, replaced with 200 ml of dichloromethane and the mixture is washed with water and with saturated aqueous sodium chloride solution. The aqueous phase is dried over sodium sulfate and filtered, and the solvent is evaporated off. The product is crystallized from dichloromethane. 14 g of the title product are obtained in the form of a white solid.

Workup

  1. customtransferred into a separating funnel
  2. customThe aqueous phase is separated out
  3. customthe organic phase is placed in a round-bottomed flask
  4. stirringthe mixture is stirred for one hour
  5. concentrationThe mixture is then concentrated under vacuum and 200 ml of methanol
  6. additionare added
  7. stirringThe mixture is stirred for 4 hours at room temperature
  8. customthe solvent is then evaporated off
  9. washthe mixture is washed with water and with saturated aqueous sodium chloride solution
  10. dry with materialThe aqueous phase is dried over sodium sulfate
  11. filtrationfiltered
  12. customthe solvent is evaporated off
  13. customThe product is crystallized from dichloromethane

Sources & evidence

ORD record
ord-878d187daf304f28bd463486c183dc6b
Source dataset
uspto-grants-2002_07
Patent number
US06417222B1

Reaction notes

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