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

HRID 591863

반응식

HRID 591863 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
150 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-e939b15943194a47b7530321302338fb
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238640B2

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