Methylamine → 4-bromo-N,2-dimethylbenzamide

N,N-Dimethylformamide (10 uL) was added to a mixture of 4-bromo-2-methylbenzoic acid (1.0 g, 0.0046 mol) in oxalyl chloride (2.0 mL, 0.023 mol). The mixture was stirred at r.t. overnight. The volatiles were removed under reduced pressure. The residue was dissolved in methylene chloride (2 mL). To the solution was added to a mixture of methylamine (0.41 mL, 0.0093 mol) and triethylamine (1.3 mL, 0.0093 mol) in DCM (10 ml). After 30 min, the reaction mixture was quenched with aqueous sodium carbonate (10 mL) and extracted with DCM (3×20 mL). The organic layers were washed with brine, dried over Na2SO4, filtered. The solvents were removed under reduced pressure to give a crude product (980 mg, 92.4%). LCMS (M+H)+: m/z=228.1/230.2.

1. customThe volatiles were removed under reduced pressure
2. dissolutionThe residue was dissolved in methylene chloride (2 mL)
3. waitAfter 30 min
4. customthe reaction mixture was quenched with aqueous sodium carbonate (10 mL)
5. extractionextracted with DCM (3×20 mL)
6. washThe organic layers were washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. customThe solvents were removed under reduced pressure

ORDレコード

ord-6dbd51bc16824583a77b77e87394c7d1

出典データセット

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08436008B2