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

HRID 980892노트

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HRID 980892 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매2회HCID 14798Sodium Hydroxide용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-60c51dc23ab6456e9a43eccd9a16f137
출처 데이터셋
uspto-grants-1987_01
특허 번호
US04639518

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