p-Toluenesulfonic acid → 2-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-5-methoxy-3H-quinazolin-4-one

HRID 591714노트

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HRID 591714 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([NH2:6])=[O:5].[OH:13][CH2:14][CH2:15][O:16][C:17]1[C:24]([CH3:25])=[CH:23][C:20]([CH:21]=O)=[CH:19][C:18]=1[CH3:26].OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[OH:13][CH2:14][CH2:15][O:16][C:17]1[C:24]([CH3:25])=[CH:23][C:20]([C:21]2[NH:6][C:4](=[O:5])[C:3]3[C:2](=[CH:10][CH:9]=[CH:8][C:7]=3[O:11][CH3:12])[N:1]=2)=[CH:19][C:18]=1[CH3:26]

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 122648142-Amino-6-methoxybenzamideHCID 23665763Sodium BisulfiteHCID 289325784-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde

생성물 1

HCID 1360380042-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-5-methoxy-3H-quinazolin-4-one

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
115 °C

실험 절차

To a solution of 2-amino-6-methoxy-benzamide (1.00 g, 6.01 mmol) and 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (1.28 g, 6.59 mmol) in N,N-dimethylacetamide (15 mL) were added NaHSO3 (58.5 wt %, 0.68 g, 6.50 mmol) and p-TSA (0.23 g, 1.20 mmol) and the reaction mixture was heated at 115° C. for 20 hours, and cooled to room temperature. N,N-dimethylacetamide was removed under reduced pressure. The residue was diluted with water (50 mL), stirred for 30 minutes, and then filtered. The solid was suspended in dichloromethane (30 mL), stirred for 1 h, filtered, and dried under vacuum to give 2-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-5-methoxy-3H-quinazolin-4-one as an off-white solid. Yield: 1.1 g (55%).

후처리

  1. temperaturecooled to room temperature
  2. customN,N-dimethylacetamide was removed under reduced pressure
  3. additionThe residue was diluted with water (50 mL)
  4. filtrationfiltered
  5. stirringstirred for 1 h
  6. filtrationfiltered
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-307d8d6ba4044e98a6195850d6139bf0
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238640B2

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