Methanamine, N-methoxy-, hydrochloride (1:1) → 3-Bromo-N-methoxy-N-methyl-5-(pentafluorosulfanyl)benzamide
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5](O)=[O:6].Cl.[CH3:18][NH:19][O:20][CH3:21].CCN(C(C)C)C(C)C>S(Cl)(Cl)=O.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([N:19]([O:20][CH3:21])[CH3:18])=[O:6]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
3-Bromo-5-(pentafluorosulfanyl)benzoic acid (1.35 g) was dissolved in thionyl chloride (10 ml) while stirring, and kept under reflux with exclusion of moisture for 5 h. Then the thionyl chloride was drawn off, the residue was taken up in DCM (40 ml) and the solution was admixed with N,O-dimethylhydroxylamine hydrochloride (381 mg). Subsequently Hünig's base (0.7 ml) was added and then the mixture was stirred for 2 h. Thereafter, the mixture was dried, the residue was taken up with EA and the solution was washed five times with water. The EA phase was dried over magnesium sulfate, filtered and concentrated. The residue was purified using silica gel (60 g cartridge, 4:1 n-heptane/EA). 1.1 g of the title compound were obtained.
Workup
- temperatureunder reflux with exclusion of moisture for 5 h
- stirringthe mixture was stirred for 2 h
- customThereafter, the mixture was dried
- washthe solution was washed five times with water
- dry with materialThe EA phase was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified
Sources & evidence
- ORD record
- ord-9da0dae061a34660bdf2b7b8c442838a
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466169B2
Reaction notes
Loading…