Oxalyl chloride → HCID 15010821, compound

HRID 373828Notes

Reaction equation

HRID 373828 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-8746a5bc77ae46b0b888571468b2da66
Source dataset
uspto-grants-1992_11
Patent number
US05166172

Reaction notes

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