Water → N-(1-benzyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide

HRID 2290585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2290585
[CH3:1][CH:2]1[CH2:6][C:5]2[CH:7]=[C:8]([S:15](=[O:18])(=[O:17])[NH2:16])[CH:9]=[C:10]([C:11]([O:13]C)=O)[C:4]=2[O:3]1.[CH2:19]([N:26]1[CH2:30][CH2:29][CH2:28][CH:27]1[CH2:31][NH2:32])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>C(O)COCCO>[CH2:19]([N:26]1[CH2:30][CH2:29][CH2:28][CH:27]1[CH2:31][NH:32][C:11]([C:10]1[C:4]2[O:3][CH:2]([CH3:1])[CH2:6][C:5]=2[CH:7]=[C:8]([S:15](=[O:18])(=[O:17])[NH2:16])[CH:9]=1)=[O:13])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 9855700(1-Benzylpyrrolidin-2-yl)methanamineHCID 13420574Methyl 2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylate

Produkt 1

HCID 13420580N-(1-benzyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8117Diethylene GlycolLösungsmittel

Versuchsvorschrift

A suspension of 4.0 g of methyl 2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylate and 3.37 g of 1-benzyl-2-aminomethyl-pyrrolidine in 15 ml of diethylene glycol is heated at 120°-130° C. and stirred for 30-31 hours. The reaction solution is cooled to room temperature, poured into 150-200 ml of water, and extracted with ethyl acetate three times. The ethyl acetate extract is washed with water followed by sodium chloride saturated water. The product is dried over magnesium sulfate and the solvent is distilled off under diminished pressure. The resulting residue is recrystallized from isopropanol by the use of decolorizing charcoal to give crystals of N-(1-benzyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide, m.p. 161°-167° C.

Aufarbeitung

  1. temperatureis heated at 120°-130° C.
  2. extractionextracted with ethyl acetate three times
  3. extractionThe ethyl acetate extract
  4. washis washed with water
  5. dry with materialThe product is dried over magnesium sulfate
  6. distillationthe solvent is distilled off under diminished pressure
  7. customThe resulting residue is recrystallized from isopropanol by the use of decolorizing charcoal

Quellen und Nachweise

ORD-Eintrag
ord-21eed971a82948048db984fbff9b4ff8
Quelldatensatz
uspto-grants-1986_10
Patentnummer
US04617314

Notizen zur Reaktion

Wird geladen…