Dimethylformamide → 4-cyano-2-fluoro-N-methylbenzamide

HRID 389090

반응식

HRID 389090 반응식
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[C:5]([F:12])[CH:4]=1)#[N:2].C1C=CC2N(O)N=[N:19][C:17]=2C=1.CN(C=O)C.CN.C1COCC1>O>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:19][CH3:17])=[O:8])=[C:5]([F:12])[CH:4]=1)#[N:2]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 5906594-Cyano-2-fluorobenzoic acidHCID 66615946Methylamine tetrahydrofuran

생성물 1

HCID 582440844-cyano-2-fluoro-N-methylbenzamide수율 79.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

4-cyano-2-fluorobenzoic acid (1.20 g), HOBt (1.47 g), WSC•monohydrochloride (2.10 g) and DMF (20 ml) were mixed with one another and stirred for 30 minutes. 2M methylamine-THF solution (11 ml) was added thereto, followed by stirring for 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and then saturated brine in this order, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1). The resulting solid was washed with n-hexane, to obtain 4-cyano-2-fluoro-N-methylbenzamide (1.03 g) as a white solid.

후처리

  1. stirringby stirring for 30 minutes
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialsaturated brine in this order, and dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1)
  7. washThe resulting solid was washed with n-hexane

출처 및 근거

ORD 기록
ord-c110b1dcb85d4aa6958b6885c203ae65
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377923B2

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