Methanamine, N-methoxy-, hydrochloride (1:1) → 5-Bromo-2-chloro-N,3-dimethoxy-N-methylbenzamide

HRID 576332Notes

Reaction equation

HRID 576332 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].Cl.[CH3:15][NH:16][O:17][CH3:18]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([N:16]([O:17][CH3:18])[CH3:15])=[O:8]

Participants

4

Reactant 2

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 867140435-Bromo-2-chloro-3-methoxybenzoyl chloride

Product 1

HCID 867140445-Bromo-2-chloro-N,3-dimethoxy-N-methylbenzamideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of acid chloride 59 (3.41 g, 14.3 mmol) in CH2Cl2 (70 mL) was added dropwise N,O-dimethylhydroxylamine hydrochloride (4.18 g, 42.9 mmol) at 0° C. under an atmosphere of nitrogen. Then, TEA (12.0 mL, 85.8 mmol) was added to the mixture at 0° C. After being stirred for 18 hours, the mixture was partitioned between EtOAc (150 mL) and water (100 mL). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the product 60 (3.45 g, 80%) as a white solid.

Workup

  1. customthe mixture was partitioned between EtOAc (150 mL) and water (100 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-126abd24411a41fa83edc91d8f1b3539
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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