Hydrochloric Acid → 3-Methanesulfonylamino-4-(2-morpholinoethoxy)benzaldehyde
Reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:5]=[CH:6][C:7]([O:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[C:8]([CH:10]=1)[NH2:9].[CH3:22][S:23](Cl)(=[O:25])=[O:24].N1C=CC=CC=1.Cl.C(=O)([O-])O.[Na+]>ClCCl>[CH3:22][S:23]([NH:9][C:8]1[CH:10]=[C:4]([CH:5]=[CH:6][C:7]=1[O:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[CH:3]=[O:2])(=[O:25])=[O:24]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 5-dimethoxymethyl-2-(2-morpholinoethoxy)aniline obtained in Step 3 (0.27 g, 0.91 mmol) in dichloromethane (2.00 mL) was added with methanesulfonyl chloride (0.11 mL, 1.42 mmol) and pyridine (0.50 mL, 6.18 mmol), followed by stirring at room temperature for 10 hours. The reaction mixture was added with hydrochloric acid (3 mol/L, 3.00 mL), was stirred at room temperature for 20 minutes, was neutralized with a saturated aqueous sodium hydrogencarbonate solution (50 ml) and was extracted with ethyl acetate (50 mL×3). The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. the crude product was purified by silica gel column chromatography (chloroform, then methanol/chloroform=1/6) to obtain 3-methanesulfonylamino-4-(2-morpholinoethoxy)benzaldehyde (0.28 g, 95%).
Workup
- stirringwas stirred at room temperature for 20 minutes
- extractionwas extracted with ethyl acetate (50 mL×3)
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customthe crude product was purified by silica gel column chromatography (chloroform
Sources & evidence
- ORD record
- ord-11ad16615ad24fb1b995aeb88a331d3f
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07470717B2
Reaction notes
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