Benzoic Acid → 2-(Dimethylamino)-2-oxoethyl benzoate

HRID 1461115Notes

Reaction equation

HRID 1461115 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13].[I-].[Na+].C(N(CC)CC)C>CN(C)C=O.O>[C:1]([O:9][CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 5238Sodium IodideHCID 8471TriethylamineHCID 758862-chloro-N,N-dimethylacetamide

Product 1

HCID 140330462-(Dimethylamino)-2-oxoethyl benzoateYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Benzoic acid (2.44 g, 0.02 mole) and 2-chloro-N,N-dimethylacetamide (2.43 g, 0.02 mole) were dissolved in 10 ml of N,N-dimethylformamide. Sodium iodide (150, 2 mmol) and triethylamine (2.02 g, 0.02 mole) were added and the mixture was stirred at room temperature (20°-25° C.) overnight. After addition of 50 ml of water the reaction mixture was extracted twice with ethyl acetate. The combined extracts were washed with a diluted solution of sodium thiosulphate, a 2% aqueous solution of sodium bicarbonate, water, dried over anhydrous sodium sulphate and evaporated in vacuo. The residue was crystallized from ethanol-water to give 3.5 g (85%) of the title compound. Mp 81°-82° C.

Workup

  1. extractionwas extracted twice with ethyl acetate
  2. washThe combined extracts were washed with a diluted solution of sodium thiosulphate
  3. dry with materiala 2% aqueous solution of sodium bicarbonate, water, dried over anhydrous sodium sulphate
  4. customevaporated in vacuo
  5. customThe residue was crystallized from ethanol-water

Sources & evidence

ORD record
ord-9a52d4f9512544d29603aae1462fe6fa
Source dataset
uspto-grants-1991_12
Patent number
US05073641

Reaction notes

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