2,4-Difluorobenzonitrile → HCID 66604568, compound

HRID 2410892Notes

Reaction equation

HRID 2410892 reaction equation
CC([O-])(C)C.[K+].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[O:15])=[CH:10][CH:9]=1.F[C:23]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:24]=1[C:25]#[N:26]>CS(C)=O.C(OCC)(=O)C>[F:31][C:29]1[CH:30]=[CH:23][C:24]([C:25]#[N:26])=[C:27]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)=[O:15])=[CH:12][CH:13]=2)[CH:28]=1

Participants

6

Reactant 3

HCID 775452,4-DifluorobenzonitrileHCID 5778154-(Morpholine-4-carbonyl)anilineHCID 23665647Potassium tert-butoxide

Product 1

HCID 66604568HCID 66604568, compoundYield 108.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

KOtBu (0.968 g, 8.63 mmol) was dissolved into DMSO (3 ml) in a 100 ml round bottom flask. (4-aminophenyl)(morpholino)methanone (1.631 g, 7.91 mmol) in 7 ml of DMSO was added. The mixture was stirred for 15 mins at r.t. 2,4-difluorobenzonitrile (1 g, 7.19 mmol) in 3 ml DMSO was added slowly into the mixture for about 5 mins. The resulting mixture was stirred for 1.5 hrs at r.t. The mixture was diluted with ethyl acetate and extracted with aqueous NH4Cl solution. The organic layer was then washed with water (4×), brine, dried with MgSO4 and concentrated. 2.54 g crude 4-fluoro-2-(4-(morpholine-4-carbonyl)phenylamino)benzonitrile (80% by LC/MS) was obtained. MS (ESI) m/z 326.11 (M+H)+.

Workup

  1. stirringThe resulting mixture was stirred for 1.5 hrs at r.t
  2. extractionextracted with aqueous NH4Cl solution
  3. washThe organic layer was then washed with water (4×), brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b32e497637394db0b2fe3d26e51c061f
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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