Oxalyl chloride → HCID 15010821, compound

HRID 1646553Notes

Reaction equation

HRID 1646553 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 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-e8f13d73b6764a40861103cf75b9ddc0
Source dataset
uspto-grants-1993_01
Patent number
US05180738

Reaction notes

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