Methylamine → 5-Bromo-2-ethoxy-N,4-dimethylbenzamide

HRID 1295922Notes

Reaction equation

HRID 1295922 reaction equation
[Br:1][C:2]1[C:3]([CH3:14])=[CH:4][C:5]([O:11][CH2:12][CH3:13])=[C:6]([CH:10]=1)[C:7](O)=[O:8].[CH3:15][NH2:16].C(OCC)(=O)C>O1CCCC1.C(N(CC)CC)C.ClC(OCC)=O>[CH3:15][NH:16][C:7](=[O:8])[C:6]1[CH:10]=[C:2]([Br:1])[C:3]([CH3:14])=[CH:4][C:5]=1[O:11][CH2:12][CH3:13]

Participants

7

Reactant 3

HCID 6329MethylamineHCID 8857Ethyl AcetateHCID 22929762HCID 22929762, compound

Product 1

HCID 229298455-Bromo-2-ethoxy-N,4-dimethylbenzamide

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 10928Ethyl chloroformateSolvent

Procedure

After dissolving 5-bromo-2-ethoxy-4-methylbenzoic acid in tetrahydrofuran (80 ml), triethylamine (3.5 ml) and ethyl chloroformate (2.4 ml) were added while cooling on ice, the mixture was stirred for 1 hour, and then a 40% methylamine aqueous solution (3.5 ml) was added. The reaction mixture was stirred for 1 hour, ethyl acetate was added and the mixture was washed with brine, after which the organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The crystals of the residue were washed with hexane and filtered to yield the title compound (5.08 g) as white crystals.

Workup

  1. additionwere added
  2. temperaturewhile cooling on ice
  3. stirringThe reaction mixture was stirred for 1 hour
  4. washthe mixture was washed with brine
  5. dry with materialafter which the organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. washThe crystals of the residue were washed with hexane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-5de0f3fe9e4c45a9924d44fcaebdefbe
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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