Oxalyl chloride → 4-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride
Reaction equation
[Na].[CH3:2][C:3]1[CH:12]=[C:11]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([OH:24])(=O)=[O:22])=[CH:17][CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.C(Cl)(=O)C([Cl:28])=O>CN(C)C=O.ClCCl>[ClH:28].[CH3:2][C:3]1[CH:12]=[C:11]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([Cl:28])(=[O:24])=[O:22])=[CH:17][CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -10 °C
Procedure
76 g (216 mmol) of the sodium salt of 4-(2-methylquinolin-4-ylmethoxy)benzenesulfonic acid in 500 ml of dimethylformamide are added dropwise to a solution of 55 ml (649 mmol) of oxalyl chloride in 100 ml of dichloromethane, cooled beforehand to −10° C. After the addition, the reaction medium is stirred at ambient temperature for 18 h. The reaction medium is then poured into 11 of ice and then extracted with ethyl acetate. The organic phases are combined, washed with water and then with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated under vacuum. 77 g (92%) of 4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride are obtained in the form of a beige solid.
Workup
- additionAfter the addition
- additionThe reaction medium is then poured into 11 of ice
- extractionextracted with ethyl acetate
- washwashed with water
- dry with materialwith a saturated aqueous solution of sodium chloride, dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-3d6d395d09a94c4fb946ac3ffac1571b
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633196B2
Reaction notes
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