Methylamine → 4-bromo-N,2-dimethylbenzamide

HRID 2090473Notes

Reaction equation

HRID 2090473 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([CH3:11])[CH:3]=1.C(Cl)(=O)C(Cl)=O.CN.[CH2:20]([N:22](CC)CC)C>C(Cl)Cl.CN(C)C=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:22][CH3:20])=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 575165344-bromo-N,2-dimethylbenzamideYield 93.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6dbd51bc16824583a77b77e87394c7d1
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

Loading…