1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-Bromo-2-fluoro-N-methoxy-N-methylbenzamide
Reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([F:11])[CH:3]=1.Cl.[CH3:13][O:14][NH:15]OOC.[CH:19]1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)C(C)C)C.CCN=C=NCCCN(C)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:15]([O:14][CH3:13])[CH3:19])=[O:7])=[C:4]([F:11])[CH:3]=1Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 4-bromo-2-fluorobenzoic acid (10 g) in DMF (4.0 mL) were added N,O-dimethoxyhydroxylamine monohydrochloride (5.3 g), HOBt (8.0 g), N-ethyldiisopropylamine (23 mL) and WSC (11 g), and the mixture was stirred at room temperature for 9 hr, and then at 40° C. for 38 hr. The reaction mixture was allowed to cool to room temperature, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with 1N aqueous sodium hydroxide solution, water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (13 g). 1H NMR (300 MHz, CDCl3) δ 3.35 (3H, s), 3.55 (3H, brs), 7.29-7.40 (3H, m).
Workup
- waitat 40° C. for 38 hr
- temperatureto cool to room temperature
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with 1N aqueous sodium hydroxide solution, water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-4ba80ddf4f8649f9985788218e356758
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901309B2
Reaction notes
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