Thionyl Chloride → 3-Dimethylamino-N-methoxy-N-methyl-5-pentafluorosulfanylbenzamide
Reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([S:12]([F:17])([F:16])([F:15])([F:14])[F:13])[CH:11]=1)[C:6](O)=[O:7].S(Cl)(Cl)=O.Cl.[CH3:24][NH:25][O:26][CH3:27].CCN(C(C)C)C(C)C>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][N:2]([CH3:18])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([S:12]([F:14])([F:17])([F:16])([F:13])[F:15])[CH:11]=1)[C:6]([N:25]([O:26][CH3:27])[CH3:24])=[O:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
3-Dimethylamino-5-pentafluorosulfanylbenzoic acid (1.0 g) was dissolved in methylene chloride (60 ml). Thionyl chloride (5 ml) was added while stirring and the mixture was stirred at RT for 2 h. To complete the reaction, the mixture was subsequently heated to reflux for 3 h. After cooling, the solvent was drawn off, the residue was dissolved in methylene chloride (50 ml), and N,O-dimethylhydroxylamine hydrochloride (315 mg) and Hünig's base (1 ml) were added. After stirring for one hour, the solvent was drawn off, and the residue was taken up with ethyl acetate and washed 5 times with water. The organic phase was dried with magnesium sulfate, filtered and concentrated. 980 mg of the title compound were obtained, which were converted directly in the next stage.
Workup
- stirringthe mixture was stirred at RT for 2 h
- customthe reaction
- temperaturethe mixture was subsequently heated
- temperatureto reflux for 3 h
- temperatureAfter cooling
- stirringAfter stirring for one hour
- washwashed 5 times with water
- dry with materialThe organic phase was dried with magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c05f2a59be234c6ba7eb3a8b733f80ad
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466169B2
Reaction notes
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