p-Toluenesulfonic acid → 2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-7-methoxyquinazolin-4(3H)-one

HRID 591725노트

반응식

HRID 591725 반응식
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][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][C:9]([O:11][CH3:12])=[CH:8][CH:7]=3)[N:1]=2)=[CH:19][C:18]=1[CH3:26]

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 140230022-Amino-4-methoxybenzamideHCID 23665763Sodium BisulfiteHCID 289325784-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde

생성물 1

HCID 1362740472-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-7-methoxyquinazolin-4(3H)-one

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
115 °C

실험 절차

To a solution of 2-amino-4-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 stirred at 115° C. for 16 hours, and cooled to room temperature. Solvent 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 hour, filtered, and dried under vacuum, to give 2-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-7-methoxy-3H-quinazolin-4-one as an off-white solid. Yield: 1.20 g (58%).

후처리

  1. temperaturecooled to room temperature
  2. customSolvent was removed under reduced pressure
  3. additionThe residue was diluted with water (50 mL)
  4. stirringstirred for 30 minutes
  5. filtrationfiltered
  6. stirringstirred for 1 hour
  7. filtrationfiltered
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-31ac56b2880f4ce68bb5272b6a9121f7
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238640B2

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