Carbon Dioxide → HCID 83909698, compound

HRID 429056Notes

Reaction equation

HRID 429056 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]1([C:14](=[O:15])NC(=O)[NH:11]1)[CH2:6][CH2:5]2.O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C(=O)=[O:30]>O>[NH2:11][C:7]1([C:14]([OH:15])=[O:30])[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 56647064HCID 56647064, compoundHCID 131722985HCID 131722985, compound

Product 1

HCID 83909698HCID 83909698, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

A mixture of (+/−)-5′-chloro-spiro[imidazolidine-4,1′indan]-2,5-dione (473 mg, 2 mmol) in water (55 mL) containing barium hydroxide nonahydrate (3.06 gm, 10 mmol) was sealed in a screw-top vessel and heated at 120° C. for 22 hours. The reaction suspension was cooled, the vessel opened and the mixture diluted to ˜200 mL with water. This suspension was brought to boil and small pieces of solid carbon dioxide were added over a 1-2 hour period. The heat was removed and the suspension was filtered while still very warm. The aqueous filtrate was concentrated under vacuum and the residue redissolved in water (30 mL). A few drops of sulfuric acid were added and any suspended material removed by filtration before concentrating the aqueous solution to dryness. This residue was triturated with methanol and several crops of the crude title compound were obtained. This material was used as is.

Workup

  1. customwas sealed in a screw-top vessel
  2. temperatureThe reaction suspension was cooled
  3. customThe heat was removed
  4. filtrationthe suspension was filtered
  5. temperaturewhile still very warm
  6. concentrationThe aqueous filtrate was concentrated under vacuum
  7. dissolutionthe residue redissolved in water (30 mL)
  8. additionA few drops of sulfuric acid were added
  9. customany suspended material removed by filtration
  10. concentrationbefore concentrating the aqueous solution to dryness
  11. customThis residue was triturated with methanol and several crops of the crude title compound
  12. customwere obtained

Sources & evidence

ORD record
ord-0ab401f9de1f401b9ff55d37c09c60e0
Source dataset
uspto-grants-2001_11
Patent number
US06316437B1

Reaction notes

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