Urea → HCID 178487123, Verbindung

HRID 470322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 470322
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH2:8][CH2:7][CH2:6]2.[NH2:14][C:15]([NH2:17])=[O:16].[CH2:18](OC(OCC)OCC)C>CS(O)(=O)=O.C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:9]3[N:17]=[C:15]([OH:16])[N:14]=[CH:18][C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=1

Komponenten

6

Edukt 3

HCID 1176UreaHCID 141126-Methoxy-alpha-tetraloneHCID 31214Ethyl orthoformate

Produkt 1

HCID 178487123HCID 178487123, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6395Methanesulfonic AcidKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 6-Methoxy-3,4-dihydro-2H-naphthalen-1-one (90 g, 0.511 M), urea (30.7 g, 0.511 M), triethylorthoformate (159 g, 1.07 M), ethanol (300 ml) and methane sulfonic acid (300 drops) was heated in the microwave at 90° C. for 1 hr. then cooled to room temperature. The solvent was removed under reduced pressure and the residue dried under vaccuo. The solid residue was then suspended in ethanol (250 ml) cooled to 0° C. and the precipitate was isolated via filtration and washed with ethanol (2×50 ml) and dried in vaccuo to give 8-Methoxy-5,6-dihydro-benzo[h]quinazolin-2-ol (43.95 g, 38% yield as a 1:1 urea complex) ES-MS MH+ 229.3 1H NMR (300 MHz, ppm, DMSO-d6): 11.45 (br S, 1H), 8.08 (d, 1H), 7.76 (br S, 1H), 6.95 (d, 1H), 6.91 (s, 1H), 5.4 (br S, 6H), 3.83 (s, 3H), 2.85 (m, 2H), 2.66 (m, 2H).

Aufarbeitung

  1. temperaturethen cooled to room temperature
  2. customThe solvent was removed under reduced pressure
  3. customthe residue dried under vaccuo
  4. temperaturecooled to 0° C.
  5. customthe precipitate was isolated via filtration
  6. washwashed with ethanol (2×50 ml)
  7. customdried in vaccuo

Quellen und Nachweise

ORD-Eintrag
ord-ce6acb0576e242798452f72656c31a91
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629147B2

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