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

HRID 1690176노트

반응식

HRID 1690176 반응식
[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]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2734985Sodium chlorodifluoroacetateHCID 178502672HCID 178502672, 화합물

생성물 1

HCID 86639409N-methoxy-N-methyl-2-difluoromethoxynicotinamide수율 53.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e4dd9a58e3b047ec9e54933ba1947e39
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153634B2

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