Acetyl chloride → N-(2-Bromo-5-chloro-4-methoxyphenyl)acetamide

HRID 1991089Notes

Reaction equation

HRID 1991089 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([Cl:11])=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20].C([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([Cl:11])=[CH:5][C:3]=1[NH:4][C:19](=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 451567062-Bromo-5-chloro-4-methoxybenzenamine

Product 1

HCID 68535198N-(2-Bromo-5-chloro-4-methoxyphenyl)acetamideYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.40 g (18.6 mmol) 2-Bromo-5-chloro-4-methoxy-aniline and 3.1 ml (22.0 mmol) triethylamine were dissolved in 50 ml THF. 1.42 ml (20.0 mmol) acetylchloride were added dropwise at room temperature. The reaction mixture was stirred at room temperature for additional 2 hours, saturated NaHCO3 solution was added and the mixture was extracted with ethyl acetate. Removal of the solvent and crystallisation with ether gave 3.6 g (12.9 mmol, 69%) of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customRemoval of the solvent and crystallisation with ether

Sources & evidence

ORD record
ord-7277291a1405423487eb8888b8c9f8f1
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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