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

HRID 591725

反応式

HRID 591725 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
115 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-31ac56b2880f4ce68bb5272b6a9121f7
出典データセット
uspto-grants-2016_01
特許番号
US09238640B2

関連ノート

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