3-Pyridinemethanamine → 4-Acetyl-N-pyridin-3-ylmethyl-benzenesulfonamide
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[NH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1>O1CCCC1.O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:14][CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Ex-17A: To a solution of 4-acetylbenzenesulfonyl chloride (0.50 g, 2.3 mmol) in tetrahydrofuran (10 mL) was added 3-(aminomethyl)pyridine (0.58 g, 5.7 mmol) and the reaction was stirred for 30 min at room temperature. The mixture was then diluted with water (30 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2×25 mL), dried over sodium sulfate, and the solvent was removed under reduced pressure. The resulting solid was dried in vacuo to afford 0.67 g (99%) of 4-acetyl-N-pyridin-3-ylmethylbenzenesulfonamide as a white solid, mp 143–144° C. 1H-NMR (300 MHz, CDCl3) δ 8.50–8.52 (m, 1H), 8.41 (d, 1H, J=2.7 Hz), 8.06 (d, 2H, J=8.7 Hz), 7.95 (d, 2H, J=8.4 Hz), 7.6–7.63 (m, 1H), 7.21–7.25 (m, 1H), 5.05 (brs, 1H), 4.22 (d, 2H, J=5.7 Hz), 2.66 (s, 3H). HRMS (EI) Calcd. for C14H14N2O3S: 290.0725 (M+); Found: 290.0726.
Workup
- extractionextracted with ethyl acetate (3×20 mL)
- washThe combined organic layers were washed with brine (2×25 mL)
- dry with materialdried over sodium sulfate
- customthe solvent was removed under reduced pressure
- customThe resulting solid was dried in vacuo
Sources & evidence
- ORD record
- ord-aa3508e7f7714e19bacf48366677276f
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07173129B2
Reaction notes
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