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

HRID 626178ノート

反応式

HRID 626178 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 89657356N-Methoxy-N-methyl-4-oxocyclohexanecarboxamide収率 39%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0c683d434d2342d7a29b14e05751a56a
出典データセット
uspto-grants-2016_04
特許番号
US09309211B2

反応ノート

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