Benzoyl chloride → N-(1-methyl-3-oxo-indan-5-yl)benzamide

HRID 593266

반응식

HRID 593266 반응식
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][CH:11]1[C:19]2[C:14](=[CH:15][C:16]([N+:20]([O-])=O)=[CH:17][CH:18]=2)[C:13](=[O:23])[CH2:12]1.C(N(CC)CC)C.C(OCC)(=O)C>ClCCl>[CH3:10][CH:11]1[C:19]2[C:14](=[CH:15][C:16]([NH:20][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:17][CH:18]=2)[C:13](=[O:23])[CH2:12]1

참가 물질

6

반응물 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 6007023-methyl-6-nitro-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 86703337N-(1-methyl-3-oxo-indan-5-yl)benzamide수율 87.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

As presented in the following reaction formula, a solution of benzoyl chloride (PhCOCl; 6.7 g, 0.043 mol) in dichloromethane (DCM; 20 mL) was added at 0° C. to a mixture of 3-methyl-6-nitro-2,3-dihydro-1-H-inden-1-one (7 g, 0.043 mol) and triethylamine (9.6 g, 0.095 mol) in dichloromethane (DCM; 100 mL), and the reaction mixture was stirred for 2 hours. After the completion of reaction, the mixture was washed with water (50 mL), saturated sodium hydrogen carbonate (50 mL) and saturated brine (50 mL) and then concentrated to give a crude product. The crude product was purified by silica gel (50 g) column chromatography (product of Merck Co., Ltd.) using an eluent of pentane (PE):ethyl acetate (10:1 (by volume)) to give the desired product N-(1-methyl-3-oxo-indan-5-yl)benzamide (10 g, yield: 87%) as a yellow solid.

후처리

  1. customAfter the completion of reaction
  2. washthe mixture was washed with water (50 mL), saturated sodium hydrogen carbonate (50 mL) and saturated brine (50 mL)
  3. concentrationconcentrated
  4. customto give a crude product
  5. customThe crude product was purified by silica gel (50 g) column chromatography (product of Merck Co., Ltd.)

출처 및 근거

ORD 기록
ord-5feabcee308f439686424084a76a7a3a
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242928B2

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