Dimethylformamide → N-(2-cyanophenyl)-N-methylmethanesulfonamide
Reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:10][NH:11][S:12]([CH3:15])(=[O:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[N:11]([CH3:10])[S:12]([CH3:15])(=[O:14])=[O:13])#[N:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a round bottom flask was added 2-fluoro-benzonitrile (1.0 g, 8.2 mmol), N-Methyl-methanesulfonamide (1.0 g, 9.2 mmol), potassium carbonate (1.7 g, 12 mmol) and N,N-dimethylformamide (5 mL). The mixture was heated at 80° C. for 18 hours. The mixture was cooled to room temperature and water (50 mL) was added. The mixture was extracted with ethyl acetate (75 mL). The organic layer was washed with water (2×25 mL) and saturated aqueous sodium chloride (25 mL), dried over magnesium sulfate, filtered and evaporated to a waxy solid. The recovered solid was triturated with hexane, filtered and dried. N-(2-Cyano-phenyl)-N-methyl-methanesulfonamide was isolated as a pale yellow solid (0.74 g, 42%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.72 (d, J=7.7 Hz, 1H), 7.70-7.64 (m, 1H), 7.56 (d, J=8.0 Hz, 1H), 7.47 (t, J=7.6 Hz, 1H), 3.40 (s, 3H), 3.13 (s, 3H). MS=211 (MH)+.
Workup
- temperatureThe mixture was cooled to room temperature
- extractionThe mixture was extracted with ethyl acetate (75 mL)
- washThe organic layer was washed with water (2×25 mL) and saturated aqueous sodium chloride (25 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated to a waxy solid
- customThe recovered solid was triturated with hexane
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-911835b3b54b4bd591f4d8610abaabc0
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Reaction notes
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