Water → N-methoxy-N-methyl-2-phenylbutanamide

HRID 2118210

반응식

HRID 2118210 반응식
N1C=CC=CC=1.Cl.[CH3:8][NH:9][O:10][CH3:11].[C:12]1([CH:18]([CH2:22][CH3:23])[C:19](Cl)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>C(Cl)Cl.C1COCC1>[CH3:11][O:10][N:9]([CH3:8])[C:19](=[O:20])[CH:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:22][CH3:23]

참가 물질

7

반응물 4

HCID 962WaterHCID 1049PyridineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 981732-Phenylbutyryl chloride

생성물 1

HCID 11229537N-methoxy-N-methyl-2-phenylbutanamide수율 979.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of pyridine (33.1 mL, 40.9 mmol) and N,O-dimethylhydroxylamine hydrochloride (26.0 g, 26.7 mmol) in anhydrous CH2Cl2 (300 mL) at 0° C. was added dropwise 2-phenylbutyryl chloride (37.4 g, 20.5 mmol) dissolved in THF (100 mL). The reaction mixture was stirred overnight at RT. H2O (300 mL) was added, and the mixture was extracted with CH2Cl2 (2×200 mL). The combined extracts were washed successively with 5% aqueous HCl (300 mL), 5% aqueous NaHCO3 (300 mL), H2O (300 mL), and brine (300 mL). The mixture was dried over Na2SO4, filtered, and concentrated to afford 41.6 g (98%) of 14 as a colorless oil which was used without further purification. 1HNMR (400 MHz, CDCl3): δ 0.87 (t, J=7.3 Hz, 3H), 1.74 (h, J=7.1 Hz, 1H), 2.08 (h, J=7.1 Hz, 1H), 3.14 (s, 3H), 3.46 (s, 3H), 3.88 (br s, 1H), 7.19-7.33 (m, 5H).

후처리

  1. extractionthe mixture was extracted with CH2Cl2 (2×200 mL)
  2. washThe combined extracts were washed successively with 5% aqueous HCl (300 mL), 5% aqueous NaHCO3 (300 mL), H2O (300 mL), and brine (300 mL)
  3. dry with materialThe mixture was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9e4dad0a664b471b8c53d2ab18558df0
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442833B2

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