Ethyl Acetate → Benzyl 5,6-dihydro-1-methyl-2-phenyl-4H-1,3,4-triazine-5-carboxylate

HRID 1651462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1651462
I.C[N:3]([C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[NH:6])[NH2:4].Br[C:14](=[CH2:25])[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].N12CCCC1=NCC[CH2:27]2.C(OCC)(=O)C>CN(C)C=O.C1C=CC=CC=1>[CH3:27][N:6]1[CH2:25][CH:14]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[NH:4][N:3]=[C:5]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 13327794N-methylbenzenecarboximidohydrazide hydroiodideHCID 13443472Benzyl 2-bromoprop-2-enoate

Produkt 1

HCID 23051225Benzyl 5,6-dihydro-1-methyl-2-phenyl-4H-1,3,4-triazine-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Benzenecarboximidic acid-N-methyl hydrazide monohydroiodide (0.43 g) in dry dimethylformamide (10 ml) and benzyl 2-bromo-prop-2-enoate (0.41 g) in benzene (2.5 ml) were cooled to 0° and stirred together under an atmosphere of nitrogen. A solution of 1,5-diazabicyclo[4.3.0]non-5-ene (0.4 ml) in dimethylformamide (5 ml) was added gradually and the mixture was stirred at 0° for a further 20 minutes. Ethyl acetate (100 ml) was added and the mixture was washed with brine (30 ml) and dried over magnesium sulphate. The solvent was removed at reduced pressure to yield the sub-title product (0.46 g) as an orange oil.

Aufarbeitung

  1. stirringthe mixture was stirred at 0° for a further 20 minutes
  2. washthe mixture was washed with brine (30 ml)
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was removed at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-88da4b961b824318bf89175698c207d7
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04927822

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