Ammonia → 4-Bromo-3,5-dimethoxybenzamide

HRID 1971775Notes

Reaction equation

HRID 1971775 reaction equation
[Br:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[O:13][CH3:14].C([N:17](CC)CC)C.ClC(OCC)=O.N>C(OCC)(=O)C.C1COCC1>[Br:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6]([NH2:17])=[O:7])=[CH:4][C:3]=1[O:13][CH3:14]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 27740264-Bromo-3,5-dimethoxybenzoic acid

Product 1

HCID 432368264-Bromo-3,5-dimethoxybenzamideYield 78.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-bromo-3,5-dimethoxybenzoic acid (15 g, 57.6 mmol) and THF (200 mL) were added triethylamine (9.63 mL, 69.0 mmol) and ethyl chloroformate (5.79 mL, 60.6 mmol) while stirring on ice, and the resulting mixture was stirred for 20 minutes while cooling on ice. After adding 28% aqueous ammonia to the mixture and stirring at room temperature for 2 hours, ethyl acetate was further added. After then thoroughly shaking the mixture, the organic layer was separated and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and the solvent in the filtrate was distilled off under reduced pressure. The obtained residue (solid) was washed with diethyl ether and collected by filtration to obtain the title compound (11.8 g, 45.4 mmol).

Workup

  1. stirringthe resulting mixture was stirred for 20 minutes
  2. temperaturewhile cooling on ice
  3. stirringstirring at room temperature for 2 hours
  4. stirringAfter then thoroughly shaking the mixture
  5. customthe organic layer was separated
  6. washthe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe mixture was filtered
  9. distillationthe solvent in the filtrate was distilled off under reduced pressure
  10. washThe obtained residue (solid) was washed with diethyl ether
  11. filtrationcollected by filtration

Sources & evidence

ORD record
ord-d0c4e81c168b4051bc5c609ff65270ee
Source dataset
uspto-grants-2013_04
Patent number
US08431603B2

Reaction notes

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