Ethyl isocyanate → 3-Ethyl-5,6-dimethoxyquinazolin-2,4(1H, 3H)-dione

HRID 980890노트

반응식

HRID 980890 반응식
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].C([O:8][C:9](=O)[C:10]1[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[CH:13]=[CH:12][C:11]=1[NH2:20])C>N1C=CC=CC=1.[OH-].[Na+]>[CH2:1]([N:3]1[C:9](=[O:8])[C:10]2[C:11](=[CH:12][CH:13]=[C:14]([O:18][CH3:19])[C:15]=2[O:16][CH3:17])[NH:20][C:4]1=[O:5])[CH3:2]

참가 물질

5

반응물 2

HCID 8022Ethyl isocyanateHCID 13749914Ethyl 2,3-dimethoxy-6-aminobenzoate

생성물 1

HCID 542515083-Ethyl-5,6-dimethoxyquinazolin-2,4(1H, 3H)-dione수율 80.5%

시약·촉매·용매 2

HCID 1049Pyridine용매2회HCID 14798Sodium Hydroxide용매

반응 조건

온도
0 °C

실험 절차

To ethyl isocyanate (1.65 ml, 1.48 g, 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, 20.8 mM) in pyridine (16.7 ml). The solution was stirred at 0° C. for thirty minutes, then kept at room temperature for one hour. During this time, a precipitate formed. 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 two 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 give crude product as a white solid; 3.12 g; mp 208°-211° C. Recrystallization from isopropanol (100 ml) and drying afforded the title compound as a white solid; 2.09 g; mp 212°-214° C., total yield 80.5%, CF3COOH(TMS), 7.60 (d, 1H, J7,8 =9.0 Hz, 7-H), 7.13 (d, 1H, J8,7 =9.0 Hz, 8-H), 4.20 (9, 2H, J=6.0 Hz, 9-H), 4.19 (s, 3H, 5 or 6-OCH3), 4.05 (s, 3H, 5 or 6-OCH3), 1.40 (t, 3H, J=6.0 Hz, 10-H). M+ 250.

후처리

  1. customDuring this time, a precipitate formed
  2. concentrationThe mixture was concentrated to dryness
  3. customto give an off-white solid
  4. temperatureheated
  5. temperatureat reflux for two hours
  6. customThe solvent was removed in vacuo
  7. dissolutionthe residue dissolved in H2O (150 ml)
  8. filtrationthe resulting white solid filtered
  9. washwashed with H2O (50 ml)
  10. customdried
  11. customto give crude product as a white solid
  12. customRecrystallization from isopropanol (100 ml)
  13. customdrying

출처 및 근거

ORD 기록
ord-2cc5331e6cd74d5b840e9813827467e7
출처 데이터셋
uspto-grants-1987_01
특허 번호
US04639518

반응 노트

불러오는 중…