N,O-Dimethylhydroxylamine → 4-Bromo-N-methoxy-N-methylbenzamide

HRID 336402Notes

Reaction equation

HRID 336402 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:20][NH:21][O:22][CH3:23]>C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:21]([O:22][CH3:23])[CH3:20])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14232N,O-DimethylhydroxylamineHCID 685154-Bromobenzoyl chlorideHCID 81531Diisopropylethylamine

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4-bromobenzoyl chloride (4.67 g, 21.3 mmol), diisopropylethylamine (3.78 mL, 46.8 mmol), and N,O-dimethylhydroxylamine (2.18 g, 22.3 mmol) in ethyl acetate (100 mL) was heated to 45° C. After 1 h, the reaction mixture was diluted with ethyl acetate (100 mL). The resulting solution was washed sequentially with water and saturated aqueous sodium chloride solution. The collected organic was dried over magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography (hexanes→ethyl acetate in hexanes) provided producted as a tan solid (4.12 g, 79%). LCMS (ESI) m/z: 244.

Workup

  1. washThe resulting solution was washed sequentially with water and saturated aqueous sodium chloride solution
  2. dry with materialThe collected organic was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (hexanes→ethyl acetate in hexanes)
  6. customprovided

Sources & evidence

ORD record
ord-ecc1f36555c7460298c0582c15295113
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Reaction notes

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