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Methyl iodide → n-Cyclobutyl-5-(2,6-dichloro-4-methoxymethyl-phenoxy)-2-methoxy-n-methyl-benzamide

HRID 1062477
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HRID 1062477 반응식
[CH:1]1([NH:5][C:6](=[O:27])[C:7]2[CH:12]=[C:11]([O:13][C:14]3[C:19]([Cl:20])=[CH:18][C:17]([CH2:21][O:22][CH3:23])=[CH:16][C:15]=3[Cl:24])[CH:10]=[CH:9][C:8]=2[O:25][CH3:26])[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:30]I>CN(C)C=O.Cl>[CH:1]1([N:5]([CH3:30])[C:6](=[O:27])[C:7]2[CH:12]=[C:11]([O:13][C:14]3[C:19]([Cl:20])=[CH:18][C:17]([CH2:21][O:22][CH3:23])=[CH:16][C:15]=3[Cl:24])[CH:10]=[CH:9][C:8]=2[O:25][CH3:26])[CH2:4][CH2:3][CH2:2]1
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HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22285669n-Cyclobutyl-5-(2,6-dichloro-4-methoxymethyl-phenoxy)-2-methoxy-benzamide

생성물 1

HCID 22285660n-Cyclobutyl-5-(2,6-dichloro-4-methoxymethyl-phenoxy)-2-methoxy-n-methyl-benzamide수율 89.1%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매
HCID 6228
Dimethylformamide
용매

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온도
0 °C

실험 절차

To a solution of the title compound of Step E (170 mg, 0.41 mmol) in dimethylformamide (4 ml) at 0° C. under nitrogen was added sodium hydride (60% dispersion in mineral oil, 41 mg, 1 mmol). The resulting slurry mixture was stirred at 0° C. for about 30 minutes and gradually became a brownish-yellow solution. To this solution at 0° C. was added methyl iodide (0.13 ml, 2 mmol). The resulting solution was warmed to room temperature and stirred for about 19 hours. The solution was diluted with 1N HCl (30 ml) and extracted with ethyl acetate (3×15 ml). The combined organic extracts were washed with 1N HCl (3×50 ml), brine, dried, filtered, and concentrated. The residue was purified by preparative TLC (50% ethyl acetate in hexanes) to afford the title compound (155 mg). MS (APCI+) Calc: 423.1, found: 424.0 (M+1).

후처리

  1. temperatureThe resulting solution was warmed to room temperature
  2. stirringstirred for about 19 hours
  3. extractionextracted with ethyl acetate (3×15 ml)
  4. washThe combined organic extracts were washed with 1N HCl (3×50 ml), brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by preparative TLC (50% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-88290ae02c8346c8bc6408353b7c42c0
출처 데이터셋
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06960604B2

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