Carbon Dioxide → HCID 12079073, compound

HRID 612757Notes

Reaction equation

HRID 612757 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

To a 12 liter four necked round bottom flask with a mechanical stirrer, thermometer, addition funnel and condenser, under nitrogen, was added 700 grams of (Z)-4-(tert-butylamino)-4-oxo-2-butenoic acid (4.0 moles) and 7757 grams of dichloromethane. The mixture was cooled to -5° C. and 438.6 grams of ethyl chloroformate (4.0 moles) was added. The mixture was cooled to -10° C. and 408.9 grams of triethylamine (4.0 moles) 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 3640 grams of distilled water was added. The mixture was stirred for 10 minutes, phase split, and the aqueous phase was removed. The organic phase was extracted three times with 3 L each 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 mm Hg) to give 550 grams of 5-(tert-butylimino)-2,5-dihydro-2-furanone. This material is hereinafter referred to as tert-butylisomaleimide. 13-CNMR shows this to be greater than 99% pure.

Workup

  1. temperatureThe mixture was cooled to -10° C.
  2. customremained below -7° C
  3. temperatureThe mixture was warmed to 11° C.
  4. additionwas added
  5. stirringThe mixture was stirred for 10 minutes
  6. customphase split
  7. customthe aqueous phase was removed
  8. extractionThe organic phase was extracted three times with 3 L each of distilled water
  9. dry with materialThe organic phase was dried with 275 grams of sodium sulfate
  10. filtrationfiltered
  11. customthe solvent was removed in vacuo at 30° C
  12. distillationThe residue was purified by distillation (50° C., 0.05 mm Hg)

Sources & evidence

ORD record
ord-4a08a6cc723c4f8b9f93f19253eda701
Source dataset
uspto-grants-1999_12
Patent number
US06005062

Reaction notes

Loading…