Triethylamine → N-[1-(4-Bromo-phenyl)-cyclopropanecarbonyl]-methanesulfonamide
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:18][S:19]([NH2:22])(=[O:21])=[O:20].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([NH:22][S:19]([CH3:18])(=[O:21])=[O:20])=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 1-(4-bromo-phenyl)-cyclopropanecarboxylic acid (5.0 g, 20.7 mmol) in toluene (30 mL) was slowly added thionyl chloride (17.7 mL, 243 mmol), and the reaction was refluxed for 4 hours. The mixture was concentrated, and the crude material was dissolved in toluene (50 mL). Methanesulfonamide (11.41 g, 120 mmol) was added, followed by triethylamine (15 mL), and the reaction was refluxed for 3 hours. After cooling to room temperature, the mixture was poured in CH2Cl2 (200 mL) and washed with H2O (150 mL). The organic layer was dried over MgSO4, filtered, and concentrated, and the crude material was purified by silica gel chromatography to give the title compound.
Workup
- temperaturethe reaction was refluxed for 4 hours
- concentrationThe mixture was concentrated
- dissolutionthe crude material was dissolved in toluene (50 mL)
- temperaturethe reaction was refluxed for 3 hours
- washwashed with H2O (150 mL)
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customthe crude material was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-b7c78dbd43824b898652069d02112a27
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273780B2
Reaction notes
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