2,4-Dimethoxybenzoic acid → N,N-Diethyl-2,4-dimethoxybenzamide

HRID 864725Notes

Reaction equation

HRID 864725 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.S(Cl)(Cl)=O.[CH2:18]([NH:20][CH2:21][CH3:22])[CH3:19]>>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]([N:20]([CH2:21][CH3:22])[CH2:18][CH3:19])=[O:7]

Participants

4

Reactant 3

HCID 70522,4-Dimethoxybenzoic acidHCID 8021DiethylamineHCID 24386Thionyl Chloride

Product 1

HCID 638883N,N-Diethyl-2,4-dimethoxybenzamideYield 69.9%

Conditions

Temperature
0 °C

Procedure

A solution of 50.0 g (0.27 mol) of 2,4-dimethoxybenzoic acid in 60 ml (98.0 g, 0.82 mol) of thionyl chloride was heated under reflux for three hours, then cooled, and the excess thionyl chloride distilled off. The resulting 2,4-dimethoxybenzoyl chloride was dissolved in 150 ml of MDC and the solution treated with a solution of 68 ml (48 g, 0.66 mol) of diethylamine in 500 ml of MDC, cooled to 0° C. When addition was complete the mixture was stirred for fifteen hours at ambient temperature, then washed with saturated sodium bicarbonate, water and brine and taken to dryness and the residue distilled in vacuo to give 44.78 g (69%) of 2,4-dimethoxy-N,N-diethylbenzamide, b.p. 155°-163° C./0.4 mm.

Workup

  1. temperatureunder reflux for three hours
  2. temperaturecooled
  3. distillationthe excess thionyl chloride distilled off
  4. dissolutionThe resulting 2,4-dimethoxybenzoyl chloride was dissolved in 150 ml of MDC
  5. additionWhen addition
  6. washwashed with saturated sodium bicarbonate, water and brine
  7. distillationthe residue distilled in vacuo

Sources & evidence

ORD record
ord-291830481cff4fc587bfebf6575a1179
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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