Oxalyl chloride → HCID 15010821, compound

HRID 850650Notes

Reaction equation

HRID 850650 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([NH2:8])=[O:7])=[CH:2]1.C(Cl)(=O)[C:10](Cl)=[O:11]>ClCCl>[O:1]1[CH:5]=[CH:4][C:3]([C:6]([N:8]=[C:10]=[O:11])=[O:7])=[CH:2]1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 17914258Furan-3-carboxamide

Product 1

HCID 15010821HCID 15010821, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Furancarboxamide (167 mg) was suspended in dichloromethane (10 ml), followed by addition of oxalyl chloride (0.20 ml) under ice-cooling, and the temperature of the reaction mixture was raised to room temperature. The reaction mixture was refluxed for 10 hours and the solvent was distilled off to give crude 3-furoyl isocyanate. In the same manner as in Example 8, the above product was reacted with fumagillol (213 mg) with stirring at room temperature for 30 minutes. Purification by silica gel column chromatography (eluent: n-hexane-ethyl acetate=2:1) gave colorless, powdery O-[N-(3-furoyl)carbamoyl]fumagillol (120 mg) (38% yield).

Workup

  1. temperaturecooling
  2. temperatureThe reaction mixture was refluxed for 10 hours
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-96e4acc22a1e419b904b709d5c5dc6ed
Source dataset
uspto-grants-2000_01
Patent number
US06017954

Reaction notes

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