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

HRID 2118210ノート

反応式

HRID 2118210 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 11229537N-methoxy-N-methyl-2-phenylbutanamide収率 979.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9e4dad0a664b471b8c53d2ab18558df0
出典データセット
uspto-grants-2008_10
特許番号
US07442833B2

反応ノート

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