3,5-Dimethoxybenzaldehyde → 6-amino-2-(3,5-dimethoxy-phenyl)-3H-quinazolin-4-one

HRID 591863

反応式

HRID 591863 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([O:24][CH3:25])[CH:23]=1)[CH:19]=O.S([O-])(O)=O.[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CN(C)C(=O)C>[NH2:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[C:19]([C:18]1[CH:21]=[C:22]([O:24][CH3:25])[CH:23]=[C:16]([O:15][CH3:14])[CH:17]=1)[NH:6][C:4]2=[O:5]

参加物

7

反応物 5

HCID 817473,5-DimethoxybenzaldehydeHCID 976652-Amino-5-nitrobenzamideHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 23665763Sodium Bisulfite

生成物 1

HCID 1363480626-amino-2-(3,5-dimethoxy-phenyl)-3H-quinazolin-4-one

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
150 °C

実験手順

A mixture of 2-amino-5-nitro-benzamide (1.81 g, 10.0 mmol), 3,5-dimethoxy-benzaldehyde (1.83 g, 11.0 mmol), sodium hydrogen sulfite (58.5 wt %, 3.94 g, 22.0 mmol), and p-toluenesulfonic acid monohydrate (0.38 g, 2.00 mmol) in N,N-dimethylacetamide (20 mL) was stirred at 150° C. for 17 hours under nitrogen and then cooled to room temperature. Saturated aqueous NaHCO3 (approximately 1 mL) was added. The mixture was stirred at room temperature for 2 hours, then concentrated to dryness. Water (80 mL) was added, stirred for 0.5 hours, and filtered. The solid was air dried. The crude compound was purified by column chromatography (silica gel 230-400 mesh; ethyl acetate as eluent) to give 6-amino-2-(3,5-dimethoxy-phenyl)-3H-quinazolin-4-one as a yellow solid. Yield: 1.50 g (50%).

後処理

  1. temperaturecooled to room temperature
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. concentrationconcentrated to dryness
  4. additionWater (80 mL) was added
  5. stirringstirred for 0.5 hours
  6. filtrationfiltered
  7. customdried
  8. customThe crude compound was purified by column chromatography (silica gel 230-400 mesh; ethyl acetate as eluent)

出典と根拠

ORDレコード
ord-e939b15943194a47b7530321302338fb
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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