Hydrochloric Acid → N-methoxy-N-methyl-2-difluoromethoxynicotinamide

HRID 1690176ノート

反応式

HRID 1690176 の反応式
[CH3:1][O:2][N:3]([CH3:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[OH:11].Cl[C:15]([F:20])([F:19])C([O-])=O.[Na+].[OH-].[Na+].Cl>O.CN(C)C=O>[CH3:1][O:2][N:3]([CH3:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[O:11][CH:15]([F:20])[F:19]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2734985Sodium chlorodifluoroacetateHCID 178502672HCID 178502672、化合物

生成物 1

HCID 86639409N-methoxy-N-methyl-2-difluoromethoxynicotinamide収率 53.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

N-methoxy-N-methyl-2-hydroxynicotinamide (500 mg, 2.76 mmol), sodium chlorodifluoroacetate (505 mg, 3.31 mmol), and sodium hydroxide (132 mg, 3.31 mmol) were added to N,N-dimethylformamide (1.4 mL). The resultant mixture was stirred at 125° C. overnight under an argon atmosphere. The reaction solution was cooled down to room temperature, added with 1N hydrochloric acid and water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified using preparative thin-layer chromatography (chloroform/methanol=9/1). N-methoxy-N-methyl-2-difluoromethoxynicotinamide (341 mg, yield 53%) was obtained as a yellow oil.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified

出典と根拠

ORDレコード
ord-e4dd9a58e3b047ec9e54933ba1947e39
出典データセット
uspto-grants-2012_04
特許番号
US08153634B2

反応ノート

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