Water → HCID 55300443, compound

HRID 425757Notes

Reaction equation

HRID 425757 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[CH2:5]1[C:10](=[O:11])[O:9][CH2:8][C:6]1=O.C1(C)C=CC=CC=1.O>C(O)(=O)C>[CH:1]1([NH:4][C:6]2[CH2:8][O:9][C:10](=[O:11])[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 69828CyclopropylamineHCID 521261Tetronic acid

Product 1

HCID 55300443HCID 55300443, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

At 0° C., 10.5 ml of cyclopropylamine (149.9 mmol) are added dropwise to 10.0 g of tetronic acid (99.9 mmol) in 57 ml of acetic acid, and the mixture is stirred at 120° C. for 2 h. After addition of 200 ml of toluene, the mixture is heated under reflux on a water separator for 3 hours. The reaction mixture is concentrated under reduced pressure and the residue is partitioned between 2.5 N of aqueous sodium hydroxide solution and dichloromethane. The aqueous phase is extracted a few more times with dichloromethane and the combined organic phases are dried over sodium sulphate. Concentration of the organic phase under reduced pressure and purification of the residue by recrystallization from ethanol gives 5.2 g (37% of theory) of 4-(cyclopropylamino)furan-2(5H)-one.

Workup

  1. temperaturethe mixture is heated
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. customthe residue is partitioned between 2.5 N of aqueous sodium hydroxide solution and dichloromethane
  4. extractionThe aqueous phase is extracted a few more times with dichloromethane
  5. dry with materialthe combined organic phases are dried over sodium sulphate
  6. customConcentration of the organic phase under reduced pressure and purification of the residue
  7. customby recrystallization from ethanol

Sources & evidence

ORD record
ord-2b9eab43f2af4b1f9e01f1e186940f94
Source dataset
uspto-grants-2012_01
Patent number
US08106212B2

Reaction notes

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