Carbon Dioxide → HCID 12079073, compound

HRID 2305265Notes

Reaction equation

HRID 2305265 reaction equation
[C:1]([NH:5][C:6](=[O:12])/[CH:7]=[CH:8]\[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].ClC(OCC)=O.C(N(CC)CC)C.C(=O)=O.C(=O)(O)[O-].[Na+]>O.ClCCl>[C:1]([N:5]=[C:6]1[O:12][C:9](=[O:11])[CH:8]=[CH:7]1)([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 5356375NSC55572

Product 1

HCID 12079073HCID 12079073, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

In a round bottom flask with a nitrogen atmosphere and containing a mechanical stirrer, a thermometer, an addition funnel and a condenser, was combined 700 grams (4.0 moles) of (Z)-4-(tert-butylamino)-4-oxo-2-butenoic acid and 7,757 grams dichloromethane. The mixture was cooled to −5° C. and 439 grams (4.0 moles) ethyl chloroformate (commercially available from Aldrich Chemical, Milwaukee, Wis.) was added. The mixture was cooled to −10° C. and 409 grams (4.0 moles) triethylamine (commercially available from Aldrich Chemical, Milwaukee, Wis.) was added slowly at a rate such that the temperature remained below −7° C. Stirring was continued at −5° C. for 2.5 hours during which time the evolution of carbon dioxide was observed. The mixture was warmed to 11° C. and a premix of 272 grams of sodium bicarbonate dissolved in 3,640 grams of distilled water was added. The mixture was stirred for 10 minutes, allowed to phase separate, and the aqueous phase was removed. The organic phase was extracted three times, each time with 3 liters of distilled water. The organic phase was dried with 275 grams of sodium sulfate, filtered and the solvent was removed in vacuo at 30° C. The residue was purified by distillation (50° C., 0.05 millimeters of Hg) to give 550 grams of 5-(tert-butylimino)-2,5-dihydro-2-furanone. This material is hereinafter referred to as TBIMI (tert-butylisomaleimide). 13C NMR indicated the product to be >99% pure.

Workup

  1. additionIn a round bottom flask with a nitrogen atmosphere and containing a mechanical stirrer
  2. addition) was added
  3. temperatureThe mixture was cooled to −10° C.
  4. addition) was added slowly at a rate such that the temperature
  5. customremained below −7° C
  6. temperatureThe mixture was warmed to 11° C.
  7. additionwas added
  8. stirringThe mixture was stirred for 10 minutes
  9. customseparate
  10. customthe aqueous phase was removed
  11. extractionThe organic phase was extracted three times
  12. dry with materialThe organic phase was dried with 275 grams of sodium sulfate
  13. filtrationfiltered
  14. customthe solvent was removed in vacuo at 30° C
  15. distillationThe residue was purified by distillation (50° C., 0.05 millimeters of Hg)

Sources & evidence

ORD record
ord-70f298fd51e647cfa471c8fec1b79cbe
Source dataset
uspto-grants-2002_08
Patent number
US06440573B1

Reaction notes

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