تفاعل #62377

ord-06e895fce5144a5ca92846444e67f562

معادلة التفاعل

[Cl-].[NH4+]
ammonium chloride
CCOC(=O)Cl
ethyl chloroformate
O=C(O)c1ccc(C(=O)OCc2ccccc2)o1
furan-2,5-dicarboxylic acid monobenzyl ester
N.O
ammonia water
NC(=O)c1ccc(C(=O)OCc2ccccc2)o1
title compound
NC(=O)c1ccc(C(=O)OCc2ccccc2)o1
5-Carbamoylfuran-2-carboxylic acid benzyl ester

ظروف التفاعل

درجة الحرارة
0°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.STIRRINGstirred at room temperature for 10 minutes
  2. 2
    أخرىthe reaction
  3. 3
    استخلاصAfter extracting the aqueous phase with ethyl acetate
  4. 4
    غسيلthe organic phase was washed with water and saturated brine
  5. 5
    تجفيفdried over anhydrous magnesium sulfate
  6. 6
    أخرىThe solvent was evaporated

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07429609B2uspto-grants-2008_09