Triethylamine → 4-bromo-N-(2,2-diethoxyethyl)benzamide

HRID 497219Notes

Reaction equation

HRID 497219 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][NH2:6])[CH3:2].C(N(CC)CC)C.[Br:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1>C(Cl)Cl>[Br:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH:6][CH2:5][CH:4]([O:7][CH2:8][CH3:9])[O:3][CH2:1][CH3:2])=[O:23])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 685154-Bromobenzoyl chlorideHCID 695242,2-Diethoxyethylamine

Product 1

HCID 223168934-bromo-N-(2,2-diethoxyethyl)benzamideYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of aminoacetaldehyde diethyl acetal (6.66 g, 50.0 mmol) in CH2Cl2 (100 ml) was added triethylamine (5.06 g, 50.0 mmol), 4-bromobenzoyl chloride (10.97 g, 50.0 mmol), and the mixture was stirred for 6 hours. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate. The solution was washed with 0.5N HCl aqueous solution, water, saturated NaHCO3 aqueous solution, brine, dried over MgSO4, and concentrated in vacuo. The residue was recrystallized with ethyl acetate-hexane to give title compound (10.45 g, 66% yield). 1H-NMR (CDCl3) δ: 7.65 (d, J=9 Hz, 2H), 7.58 (d, J=9 Hz, 2H), 6.35 (s, 1H), 4.61 (t, J=5 Hz, 1H), 3.81-3.69 (m, 2H), 3.64-3.53 (m, 4H), 1.24 (t, J=7 Hz, 6H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe solution was washed with 0.5N HCl aqueous solution, water, saturated NaHCO3 aqueous solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized with ethyl acetate-hexane

Sources & evidence

ORD record
ord-e6dc07e794134fa58305648c7c824862
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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