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

HRID 1597528Notes

Reaction equation

HRID 1597528 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 recystallized with ethyl acetate-hexane to give title compound (10.45 g, 66% yield).

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

Sources & evidence

ORD record
ord-e170c0151fad40a5a507b73a63b339d2
Source dataset
uspto-grants-2001_09
Patent number
US06294558B1

Reaction notes

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