Water → 4-Bromo-N-methoxy-N-methylbenzamide

HRID 394870Notes

Reaction equation

HRID 394870 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:12][NH:13][O:14][CH3:15].C(N(CC)CC)C.O>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:13]([O:14][CH3:15])[CH3:12])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 685154-Bromobenzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 109992524-Bromo-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromobenzoyl chloride (12.43 g, 56.6 mmol) and N,O-dimethyl hydroxyamine hydrochloride (8.29 g, 85.0 mmol) in CH2Cl2 (200 ml) was added triethylamine (23.7 ml, 170 mmol) at 0° C. The mixture was stirred at room temperature for 2 hours. Water (200 ml) was added and the aqueous layer was extracted with CH2Cl2 (150 ml×2). The combined organic layer was washed with 2N HCl (200 ml), saturated aqueous NaHCO3 (200 ml), and brine (200 ml), dried over Na2SO4, and concentarated in vacuo to give 14.9 g (quant.) of the title compound as a white solid.

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2 (150 ml×2)
  2. washThe combined organic layer was washed with 2N HCl (200 ml), saturated aqueous NaHCO3 (200 ml), and brine (200 ml)
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-2ef9865d47894545be7c0649b7829718
Source dataset
uspto-grants-2003_08
Patent number
US06603008B1

Reaction notes

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