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

HRID 389090

反応式

HRID 389090 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 582440844-cyano-2-fluoro-N-methylbenzamide収率 79.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c110b1dcb85d4aa6958b6885c203ae65
出典データセット
uspto-grants-2013_02
特許番号
US08377923B2

関連ノート

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