Sodium hydride → HCID 18620439, compound
Reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[H-].[Na+].[H][H].Br[C:11]1[N:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[F-].[K+]>CN1CCCC1=O.O1CCCC1>[CH3:1][S:2]([NH:5][C:11]1[N:21]=[C:20]([C:22]([F:25])([F:23])[F:24])[CH:19]=[CH:18][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:4])=[O:3]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
0.52 g of methanesulfonamide is introduced into a tetrahydrofuran suspension of 0.24 g of 55% sodium hydride in oil. After the evolution of hydrogen has ceased, 1.5 g (5 mmol) of ethyl 2-bromo-6-trifluoromethylnicotinate, 0.3 g (5.2 mmol) of potassium fluoride and a catalytic amount of crown ether and 5 ml of N-methylpyrrolidone are added and the mixture is heated at the boil for 18 hours. The reaction mixture is then partitioned between ethyl acetate and water and freed from organic neutral constituents. The aqueous phase is brought to pH 2.9, extracted 3 times with fresh ethyl acetate, dried and concentrated. A crystalline product, ethyl 2-methanesulfonylamino-6-trifluoromethylnicotinate, is obtained from ether/hexane; 1H-NMR (CDCl3): 10.48, s, NH, 8.49, d, CH, 7.38, d, CH, 4.45, q, CH2, 3.51, s, SO2CH3, 1.42 ppm, t, CH3.
Workup
- temperaturethe mixture is heated at the boil for 18 hours
- customThe reaction mixture is then partitioned between ethyl acetate and water
- extractionextracted 3 times with fresh ethyl acetate
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0b92089813034ce6aa8055234f3746c3
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06534445B1
Reaction notes
Loading…