2-amino-N-(4-isopropylphenyl)benzamide → HCID 46841009, 화합물

HRID 1846308노트

반응식

HRID 1846308 반응식
[NH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=1)=[O:5].[OH:20][CH2:21][CH2:22][O:23][C:24]1[C:31]([CH3:32])=[CH:30][C:27]([CH:28]=O)=[CH:26][C:25]=1[CH3:33]>C(O)C.[Cu](Cl)Cl>[OH:20][CH2:21][CH2:22][O:23][C:24]1[C:31]([CH3:32])=[CH:30][C:27]([C:28]2[N:6]([C:7]3[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=3)[C:4](=[O:5])[C:3]3[C:2](=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:1]=2)=[CH:26][C:25]=1[CH3:33]

참가 물질

5

반응물 2

HCID 28065462-amino-N-(4-isopropylphenyl)benzamideHCID 289325784-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde

생성물 1

HCID 46841009HCID 46841009, 화합물

시약·촉매·용매 2

HCID 24014Cupric Chloride촉매HCID 702Ethanol용매

실험 절차

To a solution of 2-amino-N-(4-isopropylphenyl)benzamide (0.400 g, 1.57 mmol) and 4-(2-hydroxyethoxy)-3,5-dimethylbenzaldehyde (0.30 g, 1.57 mmol) in anhydrous ethanol (20 mL) was added anhydrous copper (II) chloride (0.63 g, 4.71 mmol). The reaction mixture was stirred at reflux for 4 hours under nitrogen. The solvent was removed and the residue was diluted with dichloromethane (150 mL) and water (100 mL). The organic phase was separated and further washed with water (100 mL), brine (100 mL), and dried over sodium sulfate. The crude mixture was purified by column chromatography on silica gel (230-400 mesh) using hexane/ethyl acetate (1:1) as eluent to give the title compound as a white solid. Yield: 100 mg (15.6%). MP 160-162° C. 1H-NMR (400 Hz, CDCl3): δ 8.34 (d, J=7.6 Hz, 1H), 7.80 (m, 2H), 7.52 (m, 1H), 7.17 (d, J=8.4 Hz, 2H), 7.05 (d, J=8.4 Hz, 2H), 6.97 (s, 2H), 3.90 (m, 2H), 3.78 (t, J=4.8 Hz, 2H), 2.86 (m, 1H), 2.13 (s, 6H), 2.06 (t, J=6.4 Hz, 1H), 1.20 (d, J=7.2 Hz, 3H). MS (ES+) m/z: 429.52 (M+1).

후처리

  1. temperatureat reflux for 4 hours under nitrogen
  2. customThe solvent was removed
  3. additionthe residue was diluted with dichloromethane (150 mL) and water (100 mL)
  4. customThe organic phase was separated
  5. washfurther washed with water (100 mL), brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe crude mixture was purified by column chromatography on silica gel (230-400 mesh)

출처 및 근거

ORD 기록
ord-5379a414644f4ef791f40c634ade8849
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952021B2

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