Methanol → Methyl 4-(3-oxo-2,3-dihydro-1,2,4-triazin-6-yl)benzoate

HRID 607592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 607592
C(O[CH:4](OCC)[C:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)=O)C.Cl.[NH2:21][NH:22][C:23]([NH2:25])=[O:24].C(N(CC)C(C)C)(C)C.CO>ClCCCl.C(Cl)Cl>[O:24]=[C:23]1[N:25]=[CH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=2)=[N:21][NH:22]1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 11236Semicarbazide hydrochloride2×HCID 81531DiisopropylethylamineHCID 59216300Methyl 4-(diethoxyacetyl)benzoate

Produkt 1

HCID 59216301Methyl 4-(3-oxo-2,3-dihydro-1,2,4-triazin-6-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of methyl 4-(diethoxyacetyl)benzoate (15.4 g, 0.0578 mol), semicarbazide hydrochloride (7.1 g, 0.064 mol), N,N-diisopropylethylamine (12 mL, 0.069 mol) in 1,2-dichloroethane (150 mL), and methanol (2 mL) was heated at 95° C. for 4 h. To the mixture was added an additional 0.1 equivalents of semicarbazide hydrochloride. The mixture was stirred at 95° C. for 1 h. After cooling, the mixture was diluted with methylene chloride and washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was refluxed with acetic acid (100 mL) and water (1.0 mL) overnight. The mixture was concentrated to yield quantitative crude material which was directly used in the next step without further purification.

Aufarbeitung

  1. temperatureAfter cooling
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. temperatureThe residue was refluxed with acetic acid (100 mL) and water (1.0 mL) overnight
  7. concentrationThe mixture was concentrated
  8. customto yield quantitative crude material which
  9. customwas directly used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-803a4fc89e7c4ed4968ad1bda0520789
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915408B2

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