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p-Toluenesulfonic acid → 2-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-8-methoxy-3H-quinazolin-4-one

HRID 591750
ノート
印刷プレビュー

反応式

HRID 591750 の反応式
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][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](=[C:10]([O:11][CH3:12])[CH:9]=[CH:8][CH:7]=3)[N:1]=2)=[CH:19][C:18]=1[CH3:26]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 185365712-Amino-3-methoxybenzamideHCID 23665763Sodium BisulfiteHCID 289325784-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde

生成物 1

HCID 1361833842-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-8-methoxy-3H-quinazolin-4-one

試薬・触媒・溶媒 1

HCID 31374
Dimethylacetamide
溶媒

反応条件

温度
115 °C

実験手順

To a solution of 2-amino-3-methoxy-benzamide (700 mg, 4.22 mmol) and 4-(2-hydroxyethoxy)-3,5-dimethyl benzaldehyde (823 mg, 4.22 mmol) in N,N-dimethyl acetamide (10 mL) were added NaHSO3 (58.5 wt %, 841 mg, 4.64 mmol) and p-TSA (160 mg, 0.84 mmol). The reaction mixture was heated at 115° C. for 16 hours, then cooled to room temperature. Solvent was removed under reduced pressure. Water (100 mL) was added and stirred for 1 hour at room temperature. The solid separated was filtered and dried. The solid was further washed with diethyl ether to give crude product 2-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-8-methoxy-3H-quinazolin-4-one as an off-white solid. Yield: 1.2 g (84%).

後処理

  1. temperaturecooled to room temperature
  2. customSolvent was removed under reduced pressure
  3. additionWater (100 mL) was added
  4. customThe solid separated
  5. filtrationwas filtered
  6. customdried
  7. washThe solid was further washed with diethyl ether

出典と根拠

ORDレコード
ord-271d145065f848339259bb5624109642
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238640B2

反応ノート

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