Reaction #62377

Reaction equation

ammonium chloride

ethyl chloroformate

furan-2,5-dicarboxylic acid monobenzyl ester

ammonia water

→

title compound

5-Carbamoylfuran-2-carboxylic acid benzyl ester

Solvents

triethylamine

tetrahydrofuran

Conditions

Workup

1. 1
   workup.STIRRINGstirred at room temperature for 10 minutes
2. 2
   Otherthe reaction
3. 3
   ExtractionAfter extracting the aqueous phase with ethyl acetate
4. 4
   Washthe organic phase was washed with water and saturated brine
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   OtherThe solvent was evaporated

Procedure

170 mg of furan-2,5-dicarboxylic acid monobenzyl ester was dissolved in 5 mL of tetrahydrofuran, and added with 144 μl of triethylamine. After cooling to 0° C., 72.3 μl of ethyl chloroformate was added dropwise and stirred at this temperature for 30 minutes. 1 mL of concentrated ammonia water was added and stirred at room temperature for 10 minutes, and then aqueous ammonium chloride was added to stop the reaction. After extracting the aqueous phase with ethyl acetate, the organic phase was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, to afford 185 mg of the title compound as white crystals.

Source