Sulfamic Acid → Furan-2,5-dicarboxylic Acid Monobenzyl Ester

HRID 34098

Reaktionsgleichung

Reaktionsgleichung von HRID 34098
[CH2:1]([O:8][C:9]([C:11]1[O:12][C:13]([CH:16]=[O:17])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)([OH:20])N.Cl([O-])=O.[Na+].P([O-])(O)(O)=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O>[CH2:1]([O:8][C:9]([C:11]1[O:12][C:13]([C:16]([OH:20])=[O:17])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 5

HCID 5987Sulfamic AcidHCID 24477Sodium ThiosulfateHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 600347885-Formyl-2-furancarboxylic acid benzyl ester

Produkt 1

HCID 16091220Furan-2,5-dicarboxylic Acid Monobenzyl EsterAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

490 mg of 5-formylfuran-2-carboxylic acid benzyl ester was dissolved in 10 mL of acetonitrile, and added with a solution containing 413 mg of sulfamic acid in 5 mL of water. After cooling to 0° C., a solution containing 202 mg of sodium chlorite and 232 mg of potassium dihydrogen phosphate in 5 mL of water was added dropwise. After cooling at this temperature for 30 minutes, sodium thiosulfate aqueous solution was added at 0° C. to stop the reaction, and extracted with a mixture of tetrahydrofuran and ethyl acetate. The organic phase was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off to afford 520 mg of the title compound as white crystals.

Aufarbeitung

  1. additionadded with a solution
  2. additionwas added dropwise
  3. temperatureAfter cooling at this temperature for 30 minutes
  4. customthe reaction
  5. extractionextracted with a mixture of tetrahydrofuran and ethyl acetate
  6. washThe organic phase was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-c6f74879b55d4a9f9448b3912936560b
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429609B2

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