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

HRID 389090

Reaction equation

HRID 389090 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c110b1dcb85d4aa6958b6885c203ae65
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Linked notes

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