Water → N,N-diethylthiophene-3-carboxamide

HRID 235080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 235080
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.O=S(Cl)Cl.[CH2:13]([NH:15][CH2:16][CH3:17])[CH3:14].O>C(Cl)(Cl)Cl>[CH2:13]([N:15]([CH2:16][CH3:17])[C:6]([C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)=[O:8])[CH3:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6918Thiophene-3-carboxylic acidHCID 8021DiethylamineHCID 24386Thionyl Chloride

Produkt 1

HCID 11389776N,N-diethylthiophene-3-carboxamideAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of 5.0 g (39 mmol) of 3-thiophenecarboxylic acid (Aldrich Chemical Co.), to which was added 10 mL (134 mmol) of SOCl2 in 20 mL of CHCl3 was stirred at reflux for 3 hours. After cooling to room temperature, the solution was concentrated in vacuo. The residue was dissolved in 15 mL of methylene chloride, and the solution was cooled in an ice bath. To this was added dropwise 13 mL (126 mmol) of diethyl amine, and the reaction was stirred at room temperature for 1 hour. Water was added, and the mixture was extracted with methylene chloride, which was washed with aqueous NaHCO3 solution, water, and bdne, and concentrated to give 9.3 g of crude product. This material was purified by flash chromatography on silica gel, eluting with 6:1 hexane:ethyl acetate, to afford 6.34 g of the title product after removal of the solvents. NMR (CDCl3) δ:7.48 (dd, 1H, J=1, J=3 Hz), 7.32 (dd, 1H, J=3, J=6 Hz), 7.20 (dd, 1H, J=1, J=6 Hz), 3.60-3.30 (bs, 4H), 1.20 (bm, 6H).

Aufarbeitung

  1. temperatureat reflux for 3 hours
  2. concentrationthe solution was concentrated in vacuo
  3. dissolutionThe residue was dissolved in 15 mL of methylene chloride
  4. temperaturethe solution was cooled in an ice bath
  5. stirringthe reaction was stirred at room temperature for 1 hour
  6. extractionthe mixture was extracted with methylene chloride, which
  7. washwas washed with aqueous NaHCO3 solution, water, and bdne
  8. concentrationconcentrated
  9. customto give 9.3 g of crude product
  10. customThis material was purified by flash chromatography on silica gel
  11. washeluting with 6:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-01678aaaa51f4b0882703fad6e28a0cd
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05597832

Notizen zur Reaktion

Wird geladen…