Triethylamine → 6-(3,4-Dihydro-4-(3,4-dimethoxyphenylcarbonyl)-1,4(2H)-benzoxazin-6-yl)-2,3,4,5-tetrahydropyridazin-3-one

HRID 35183

Reaktionsgleichung

Reaktionsgleichung von HRID 35183
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=3)=[CH:10][C:5]=2[NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[C:30](Cl)=[O:31]>C(Cl)Cl>[CH3:25][O:26][C:27]1[CH:28]=[C:29]([C:30]([N:4]2[C:5]3[CH:10]=[C:9]([C:11]4[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=4)[CH:8]=[CH:7][C:6]=3[O:1][CH2:2][CH2:3]2)=[O:31])[CH:33]=[CH:34][C:35]=1[O:36][CH3:37]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 77070Veratroyl chlorideHCID 155994076-(3,4-Dihydro-1,4(2H)-benzoxazin-6-yl)-2,3,4,5-tetrahydropyridazin-3-one

Produkt 1

HCID 155994096-(3,4-Dihydro-4-(3,4-dimethoxyphenylcarbonyl)-1,4(2H)-benzoxazin-6-yl)-2,3,4,5-tetrahydropyridazin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

6-(3,4-Dihydro-1,4(2H)-benzoxazin-6-yl)-2,3,4,5-tetrahydropyridazin-3-one was dissolved in methylene chloride and 1.1 equivalent of triethylamine. 1.1 equivalent of 3,4-dimethoxybenzoylchloride was added and the mixture heated at reflux for four hours. The solution was washed with sodium bicarbonate solution and then evaporated to dryness. The residue was chromatographed on silica gel eluting with 1:1 ethyl acetate:ethyl ether. The title compound was collected as white needles, mp 207°-208° C.

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureat reflux for four hours
  3. washThe solution was washed with sodium bicarbonate solution
  4. customevaporated to dryness
  5. customThe residue was chromatographed on silica gel eluting with 1:1 ethyl acetate
  6. customThe title compound was collected as white needles, mp 207°-208° C.

Quellen und Nachweise

ORD-Eintrag
ord-53bea2c0b3cd48bb9625a2568a757434
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04766118

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