Ammonium Acetate → 4-(3-chlorophenyl)-6-(4-methoxybenzoyl)-2(1H)-quinazolinone

HRID 1441461노트

반응식

HRID 1441461 반응식
[NH4+:1].C([O-])(=O)C.ClC(Cl)(Cl)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:13][C:12]=1[C:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=1)=[O:9]>CS(C)=O>[Cl:34][C:30]1[CH:29]=[C:28]([C:27]2[C:12]3[C:11](=[CH:16][CH:15]=[C:14]([C:17](=[O:26])[C:18]4[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=4)[CH:13]=3)[NH:10][C:8](=[O:9])[N:1]=2)[CH:33]=[CH:32][CH:31]=1

참가 물질

4

반응물 2

HCID 517165Ammonium AcetateHCID 179760992,2,2-trichloro-N-[2-(3-chlorobenzoyl)-4-(4-methoxybenzoyl)phenyl]-acetamide

생성물 1

HCID 686894594-(3-chlorophenyl)-6-(4-methoxybenzoyl)-2(1H)-quinazolinone수율 77.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
60 °C

실험 절차

Acetic acid, ammonium salt (0.107 mol) was added at room temperature to a mixture of intermediate 12 (0.0536 mol) in DMSO (250 ml). The mixture was stirred at 60° C. for 4 hours then brought to room temperature, poured out into ice water and stirred. The precipitate was filtered, washed with water and taken up in warm CH3CN. The precipitate was filtered, washed with diethyl ether and dried under a vacuo, yielding 16.2 g (77%) of intermediate 13. The mother layer was evaporated. The residue was purified by column chromatography over silica gel (15-40 μm) (eluent: DCM/MeOH/NH4OH; 95/5/0.1). The pure fractions were collected and the solvent was evaporated. The residue (1.2 g, 6%) was crystallized from 2-propanone. The precipitate was filtered off and dried, yielding 0.9 g (4%) of 4—(3-chlorophenyl)-6-(4-methoxybenzoyl)-2(1H)quinazolinone (intermediate 13), mp. 248° C.

후처리

  1. customthen brought to room temperature
  2. stirringstirred
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. filtrationThe precipitate was filtered
  6. washwashed with diethyl ether
  7. customdried under a vacuo

출처 및 근거

ORD 기록
ord-458b67b9b60a4232ab6bc1342d0e4a4e
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07655654B2

반응 노트

불러오는 중…