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

HRID 2290583

Reaktionsgleichung

Reaktionsgleichung von HRID 2290583
[CH3:1][CH:2]1[CH2:6][C:5]2[CH:7]=[C:8]([S:14](=[O:17])(=[O:16])[NH2:15])[CH:9]=[C:10]([C:11]([OH:13])=O)[C:4]=2[O:3]1.C(N(CC)CC)C.C(Cl)(=O)OCC.[CH2:31]([N:33]1[CH2:37][CH2:36][CH2:35][CH:34]1[CH2:38][NH2:39])[CH3:32]>CN(C)C=O.CC(C)=O>[CH2:31]([N:33]1[CH2:37][CH2:36][CH2:35][CH:34]1[CH2:38][NH:39][C:11]([C:10]1[C:4]2[O:3][CH:2]([CH3:1])[CH2:6][C:5]=2[CH:7]=[C:8]([S:14](=[O:17])(=[O:16])[NH2:15])[CH:9]=1)=[O:13])[CH3:32]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 136908862-Methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid

Produkt 1

HCID 13420575N-(1-ethyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

(+)-2-Methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxylic acid [[α]D =+16.67° (dimethylformamide, c=1)], 6 g, is dissolved in a mixed solvent of 55 ml of dimethylformamide and 55 ml of acetone and 5.9 g of triethylamine is added, and the whole is stirred. Under cooling at 15° C. 2.7 g of ethyl chlorocarbonate is added dropwise for 10 minutes and the solution is stirred at room temperature for 40-45 minutes. Then, (-)-1-ethyl-2-aminomethylpyrrolidine, 7.5 g, is added and the reactant is stirred at room temperature for 20 minutes and allowed to stand overnight. Excess triethylamine and acetone are distilled off under reduced pressure and the resulting residue is poured while stirring into 500-600 ml of water. Precipitated cystals are separated by suction filtration, washed with water and dried. The filtrate, aqueous layer is extracted with ethyl acetate three times. The extract layer is washed with water and dried, and ethyl acetate is distilled off under reduced pressure to give crude crystals. Both the crude crystals are put together and recrystallized from ethyl acetate to afford crystals of N-(1-ethyl-2-pyrrolidinylmethyl)-2-methyl-5-sulfamoyl-2,3-dihydrobenzofuran-7-carboxamide, m.p. 164°-165° C., [α]D =-50.867° (dimethylformamide, c=1), which is an optically active compound.

Aufarbeitung

  1. additionis added
  2. stirringthe solution is stirred at room temperature for 40-45 minutes
  3. stirringthe reactant is stirred at room temperature for 20 minutes
  4. distillationExcess triethylamine and acetone are distilled off under reduced pressure
  5. additionthe resulting residue is poured
  6. stirringwhile stirring into 500-600 ml of water
  7. customPrecipitated cystals are separated by suction filtration
  8. washwashed with water
  9. customdried
  10. extractionThe filtrate, aqueous layer is extracted with ethyl acetate three times
  11. washThe extract layer is washed with water
  12. customdried
  13. distillationethyl acetate is distilled off under reduced pressure
  14. customto give crude crystals
  15. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ebe413b3bcf54a26939186df3746b27c
Quelldatensatz
uspto-grants-1986_10
Patentnummer
US04617314

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