Butyl isocyanate → 3-n-Butyl-5,6-dimethoxyquinazolin-2,4-(1H, 3H)-dione Hemihydrate

HRID 980892Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 980892
[CH2:1]([N:5]=[C:6]=[O:7])[CH2:2][CH2:3][CH3:4].C([O:10][C:11](=[O:23])[C:12]1[C:17]([O:18][CH3:19])=[C:16]([O:20][CH3:21])[CH:15]=[CH:14][C:13]=1[NH2:22])C>N1C=CC=CC=1.[OH-].[Na+]>[OH2:7].[CH2:1]([N:5]1[C:11](=[O:10])[C:12]2[C:13](=[CH:14][CH:15]=[C:16]([O:20][CH3:21])[C:17]=2[O:18][CH3:19])[NH:22][C:6]1=[O:7])[CH2:2][CH2:3][CH3:4].[CH2:1]([N:5]1[C:11](=[O:23])[C:12]2[C:13](=[CH:14][CH:15]=[C:16]([O:20][CH3:21])[C:17]=2[O:18][CH3:19])[NH:22][C:6]1=[O:7])[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 2

HCID 8110Butyl isocyanateHCID 13749914Ethyl 2,3-dimethoxy-6-aminobenzoate

Produkt 1

HCID 1317150493-n-Butyl-5,6-dimethoxyquinazolin-2,4-(1H, 3H)-dione Hemihydrate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To n-butyl isocyanate (2.06 g, 2.34 ml, 20.8 mM) in pyridine (9.2 ml) at 0° C. was added a cold solution of 2-amino-5,6-dimethoxybenzoic acid ethyl ester (3.0 g, 13.3 mM) in pyridine (16.7 ml). The solution was stirred at 0° C. for thirty minutes, then kept at room temperature for one hour. The mixture was concentrated to dryness to give an off-white solid. This was dissolved in 69.9 ml of 1N NaOH (4:1 MeOH-H2O) and heated at reflux for 2 hours. The solvent was removed in vacuo and the residue dissolved in H2O (150 ml). The mixture was taken to pH 6 with acetic acid and the resulting white solid filtered, washed with H2O (50 ml) and dried to afford the title compound as a white solid; 2.38 g (64.3%); mp 159°-161° C.; CDCl3 (TMS) 7.21 (d, 1H, J7,8 =9.0 Hz, 7-H), 6.82 (d, 1H, J8,7 =9.0 Hz, 8-H), 4.10 (t, 2H, J9,10 =7.0 Hz, 9-H), 3.95 (s, 3H, 5 or 6-OCH3), 3.85 (s, 3H, 5 or 6-OCH3), 0.80-2.10 (m, 7H, 10-H, 11-H, 12-H), M+ 278.

Aufarbeitung

  1. concentrationThe mixture was concentrated to dryness
  2. customto give an off-white solid
  3. temperatureheated
  4. temperatureat reflux for 2 hours
  5. customThe solvent was removed in vacuo
  6. dissolutionthe residue dissolved in H2O (150 ml)
  7. filtrationthe resulting white solid filtered
  8. washwashed with H2O (50 ml)
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-60c51dc23ab6456e9a43eccd9a16f137
Quelldatensatz
uspto-grants-1987_01
Patentnummer
US04639518

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