Acetyl chloride → N-(4-Bromo-2-ethyl-benzyl)-acetamide

HRID 2387082Notes

Reaction equation

HRID 2387082 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([CH2:10][CH3:11])[CH:3]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20]>ClCCl.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:19](=[O:21])[CH3:20])=[C:4]([CH2:10][CH3:11])[CH:3]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 58764124(4-Bromo-2-ethylphenyl)methanamine

Product 1

HCID 58764154N-(4-Bromo-2-ethyl-benzyl)-acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 4-bromo-2-ethyl-benzylamine (700 mg, 3.3 mmol) and triethylamine (600 μL, 4.3 mmol) in dichloromethane (5 mL) at room temperature was added acetyl chloride (310 μL, 4.5 mmol). The solution was stirred for 1 h, diluted in water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, then saturated sodium chloride, dried (Na2SO4), filtered, and concentrated in vacuo to an off-white solid (820 mg, 97%). 1H NMR (300 MHz, CDCl3): δ 1.20 (t, J=7.54 Hz, 3 H) 2.00 (s, 3 H) 2.62 (q, J=7.54 Hz, 2 H) 4.38 (d, J=5.46 Hz, 2 H) 5.59 (s, 1 H) 7.09 (d, J=8.10 Hz, 1 H) 7.26-7.31 (m, 1 H) 7.34 (d, J=1.88 Hz, 1 H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium bicarbonate
  3. dry with materialsaturated sodium chloride, dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to an off-white solid (820 mg, 97%)

Sources & evidence

ORD record
ord-4ebcedbd676847a5a94397b446d83c5f
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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