Triethylamine → N-Methoxy-N-methyl-4-oxocyclohexanecarboxamide

HRID 626178노트

반응식

HRID 626178 반응식
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.C(Cl)(=O)C(Cl)=O.CCN(CC)CC.Cl.[CH3:25][NH:26][O:27][CH3:28]>C(Cl)Cl.O>[CH3:28][O:27][N:26]([CH3:25])[C:8]([CH:5]1[CH2:4][CH2:3][C:2](=[O:1])[CH2:7][CH2:6]1)=[O:10]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 1927304-Oxocyclohexanecarboxylic acid

생성물 1

HCID 89657356N-Methoxy-N-methyl-4-oxocyclohexanecarboxamide수율 39%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-oxocyclohexanecarboxylic acid (4.2 g, 0.0293 mol) in CH2Cl2 (20 mL) was added oxalyl chloride (5.2 g, 0.44 mol) slowly, stirred at room temperature for 1 hour and concentrated, then 20 mL CH2Cl2 was added, followed by addition of Et3N (9 g, 0.116 mol) and N,O-dimethylhydroxylamine hydrochloride (3.5 g, 0.0359 mol). The reaction mixture was stirred for 2 hours, and then 100 mL water was added. The mixture was extracted with ethyl acetate. The extract was concentrated and purified by column chromatography to give the desired product (2.1 g, 39% yield).

후처리

  1. concentrationconcentrated
  2. addition20 mL CH2Cl2 was added
  3. stirringThe reaction mixture was stirred for 2 hours
  4. extractionThe mixture was extracted with ethyl acetate
  5. concentrationThe extract was concentrated
  6. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-0c683d434d2342d7a29b14e05751a56a
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309211B2

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