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Iodoacetamide → 2-[5-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]acetamide

HRID 2095833
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HRID 2095833 반응식
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[N:13][CH:14]=2)=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.I[CH2:38][C:39]([NH2:41])=[O:40].C(OCC)(=O)C>CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12](=[N:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[N:13]([CH2:38][C:39]([NH2:41])=[O:40])[CH:14]=2)=[CH:26][CH:27]=1
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참가 물질

7

반응물 4

HCID 3727IodoacetamideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 66968540N-{5-[(4-methoxybenzyl)oxy]pyridin-2-yl}-4-methylbenzenesulfonamide

생성물 1

HCID 669689682-[5-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]acetamide수율 299.7%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a suspension of N-{5-[(4-methoxybenzyl)oxy]pyridin-2-yl}-4-methylbenzenesulfonamide (10.0 g, 26.0 mmol) in N,N-dimethylformamide (85 mL) were added N,N-diisopropylethylamine (6.8 mL, 39.0 mmol) and iodoacetamide (5.77 g, 31.0 mmol), and the mixture was stirred at 60° C. for 5 hr. After cooling to room temperature, ethyl acetate and water were added, and the mixture was extracted 3 times with a mixed solution of ethyl acetate and tetrahydrofuran. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was washed with ethyl acetate and collected by filtration to give the title compound (34.4 g, 75%) as a white solid.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted 3 times with a mixed solution of ethyl acetate and tetrahydrofuran
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure
  7. washThe obtained residue was washed with ethyl acetate
  8. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-3fe98c128c754fca8861d1e50f5a6dc3
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08445509B2

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