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

HRID 980892ノート

反応式

HRID 980892 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒2 回HCID 14798Sodium Hydroxide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-60c51dc23ab6456e9a43eccd9a16f137
出典データセット
uspto-grants-1987_01
特許番号
US04639518

反応ノート

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