4-Amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamide → Benzo[1,3]-dioxole-5-carboxylic acid [4-(2-diethylamino-ethylcarbarnoyl)-5-methoxy-phenyl]-amide

HRID 32287

Reaktionsgleichung

Reaktionsgleichung von HRID 32287
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([O:18][CH3:19])[CH:3]=1.[CH2:20]1[O:31][C:30]2[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][C:22]=2[O:21]1>C(Cl)(Cl)Cl>[CH2:14]([N:11]([CH2:12][CH3:13])[CH2:10][CH2:9][NH:8][C:6]([C:5]1[C:4]([O:18][CH3:19])=[CH:3][C:2]([NH:1][C:25]([C:24]2[CH:28]=[CH:29][C:30]3[O:31][CH2:20][O:21][C:22]=3[CH:23]=2)=[O:26])=[CH:17][CH:16]=1)=[O:7])[CH3:15]

Komponenten

4

Edukt 2

HCID 773744-Amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamideHCID 27347491,3-Benzodioxole-5-carbonyl chloride

Produkt 1

HCID 59793341Benzo[1,3]-dioxole-5-carboxylic acid [4-(2-diethylamino-ethylcarbarnoyl)-5-methoxy-phenyl]-amideAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

200 mg (0.75 mmol) of 4-amino-N-(2-diethylamino-ethyl)-2-methoxy-benzamide in 10 ml of chloroform is mixed with 5 ml of 3,4-methylenedioxybenzoic acid chloride (in chloroform) and this mixture is stirred for 3 hours at room temperature. After concentration by evaporation in a vacuum, the residue is taken up in 40 ml of dilute sodium bicarbonate solution and then extracted with 40 ml of methylene chloride. The methylene chloride phase is washed with water, dried, filtered and concentrated by evaporation. The crude product, 315 mg, is taken up in methylene chloride and purified on silica gel. As a mobile solvent, a mixture that consists of methylene chloride/methanol (97:3→90:10) is used. 210 mg (67% of theory) of benzo[1,3]dioxole-5-carboxylic acid [4-(2-diethylamino-ethylcarbamoyl)-5-methoxy-phenyl]-amide (melting point 131.1° C.) is obtained.

Aufarbeitung

  1. concentrationAfter concentration
  2. customby evaporation in a vacuum
  3. extractionextracted with 40 ml of methylene chloride
  4. washThe methylene chloride phase is washed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. custompurified on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-edf55ea1959844a7beb69242da746a76
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427390B2

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