Triethylamine → N-(3-Bromo-4-methylphenyl)-2-methylpropanamide

HRID 1269138

Reaction equation

HRID 1269138 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].C(N(CC)CC)C.[CH3:17][CH:18]([CH3:22])[C:19](Cl)=[O:20]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:19](=[O:20])[CH:18]([CH3:22])[CH3:17])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 82187Benzenamine, 3-bromo-4-methyl-

Product 1

HCID 22048859N-(3-Bromo-4-methylphenyl)-2-methylpropanamideYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of 1.0 g (5.40 mmol) of 3-bromo-4-methylaniline and 0.91 mL (6.50 mmol) of triethylamine in 10 mL THF at 0° C. was slowly added 0.68 mL (6.50 mmol) of 2-methylpropanoyl chloride. The reaction mixture was stirred at room temperature for 2 hours and concentrated in vacuo. The residue was dissolved in CH2Cl2 and washed with H2O, followed by brine. The organic layer was dried over MgSO4 and concentrated in vacuo to give 1.37 g (5.35 mmol, 99%) of the desired product: ESMS m/e: 255.9 (M+H)+.

Workup

  1. customat 0° C.
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with H2O
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f8b3f0508964c4c920ba3f9131ed0d2
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Linked notes

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