Diethylamine → N,N-diethyl-2-methoxybenzamide

HRID 969773Notes

Reaction equation

HRID 969773 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[CH3:6][O:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](Cl)=[O:11]>C1(C)C=CC=CC=1>[CH3:6][O:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[O:11]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 889692-Methoxybenzoyl chloride

Product 1

HCID 346975N,N-diethyl-2-methoxybenzamideYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of diethylamine (25.8 g, 0.352 mol) in toluene (toluene 30.8 g) was placed in a 200-mL four-neck flask. Under cooling with ice, a solution of 2-methoxybenzoic chloride (20 g, 0.117 mol) in toluene (toluene 10.0 g) was added dropwise gradually in order to prevent sudden surge of heat. After completion of addition of the entire amount of the solution, the formed amine hydrochloride was removed through extraction with water. The thus-obtained toluene layer was dried over MgSO4, and the solvent was vaporized out, to thereby yield 22.8 g of 2-methoxy-N,N-diethylbenzamide (yield: 94%).

Workup

  1. temperatureUnder cooling with ice
  2. temperatureof heat
  3. additionAfter completion of addition of the entire amount of the solution
  4. customthe formed amine hydrochloride was removed through extraction with water
  5. dry with materialThe thus-obtained toluene layer was dried over MgSO4

Sources & evidence

ORD record
ord-941a2c7a89074de6b656e9926cbcadce
Source dataset
uspto-grants-2007_12
Patent number
US07307185B2

Reaction notes

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