Reaction equation
[NH2:1][C:2]1[C:10](C)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:12][S:13]([NH2:16])(=[O:15])=[O:14].[CH2:17](N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[NH2:1][C:2]1([CH3:17])[CH:10]=[CH:9][CH:8]=[CH:7][CH:3]1[C:4]([NH:16][S:13]([CH3:12])(=[O:15])=[O:14])=[O:6]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
20 g (128 mmol) of 2-amino-3-methylbenzoic acid are dissolved in 600 ml of dichloromethane, and 10.98 g (115 mmol) of methanesulphonamide, 24.40 g (154 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide and 15.68 g (128 mmol) of 4-(dimethylamino)pyridine are then added under argon. The reaction is stirred at room temperature for 16 h, the solvent is distilled off and the residue is taken up in ethyl acetate and water. The ethyl acetate phase is washed four times with a 1N hydrochloric acid solution and then in each case once with water and a concentrated sodium chloride solution. After drying over sodium sulphate, the desired product is obtained by chromatographic purification.
Workup
- distillationthe solvent is distilled off
- washThe ethyl acetate phase is washed four times with a 1N hydrochloric acid solution
- dry with materialAfter drying over sodium sulphate
Sources & evidence
- ORD record
- ord-309219c488304383992fdc092b007281
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658800B2
Linked notes
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