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

HRID 859691Notes

Reaction equation

HRID 859691 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-8ce2fd62d04b46c4b630752494f37a82
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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