Sodium hydride → N-Ethyl-N-[6-(((4-methoxypyridin-2-yl)methyl)oxy)-2,2-dimethylchroman-4-yl]methanesulfonamide
Reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:11][CH:10]([N:12]([CH2:17][CH3:18])[S:13]([CH3:16])(=[O:15])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:19])[CH:8]=2)[O:3]1.[H-].[Na+].Cl.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][N:29]=[C:28]([CH2:32]Cl)[CH:27]=1>CC(N(C)C)=O>[CH2:17]([N:12]([CH:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:19][CH2:32][C:28]3[CH:27]=[C:26]([O:25][CH3:24])[CH:31]=[CH:30][N:29]=3)[CH:8]=2)[O:3][C:2]([CH3:1])([CH3:20])[CH2:11]1)[S:13]([CH3:16])(=[O:15])=[O:14])[CH3:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
0.58 g (1.9 mmol) of N-[2,2-dimethyl-6-hydroxychroman-4-yl]-N-ethyl-methanesulfonamide (Example 1g) was stirred at 50° C. for 30 min with 0.15 g (5 mmol) of NaH (80%) in 40 ml of DMA. A solution of 0.4 g (2 mmol) of 4-methoxy-2-chloromethylpyridine hydrochloride in 5 ml of DMA was then added dropwise and the mixture was heated to 75° C. for 2 h. After reaction was complete, it was concentrated in vac., the residue was treated with ice water, the mixture was extracted with EA, the extract was dried and concentrated, and the residue was crystallized using diisopropyl ether. 0.5 g was obtained, m.p. 87-89° C.
Workup
- customAfter reaction
- concentrationit was concentrated in vac
- addition, the residue was treated with ice water
- extractionthe mixture was extracted with EA
- customthe extract was dried
- concentrationconcentrated
- customthe residue was crystallized
- custom0.5 g was obtained
Sources & evidence
- ORD record
- ord-ad04de4d3e4840b5810b71797efbac5b
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06177449B1
Reaction notes
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