Dimethylamine → 4-formyl-N,N-dimethylbenzamide

HRID 1577803Notes

Reaction equation

HRID 1577803 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)(O)=[O:2].O1CCCC1.[CH3:17][NH:18][CH3:19]>O>[CH:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1]([N:18]([CH3:19])[CH3:17])=[O:2])=[CH:5][CH:6]=1)=[O:9]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 120884-Formylbenzoic acid

Product 1

HCID 105592054-formyl-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 15.0 g. of 4-carboxybenzaldehyde, 17.0 g. of N,N'-carbonyldiimidazole and 150 ml. of tetrahydrofuran is allowed to stand at room temperature for one hour. Dimethylamine is passed thru the above solution for one hour and the reaction mixture is allowed to stand at room temperature for 18 hours, then is heated at reflux temperature for one hour. Water is added and the solvent is distilled off. The residue is extracted with methylenechloride. The organic layer is washed with dilute hydrochloric acid and water, dried over magnesium sulfate and concentrated to an oil. The oil is triturated with a little methylene chloride and the insoluble material is filtered off. The mother liquor is concentrated and 7.9 g. of p-formyl-N,N-dimethylbenzamide is obtained as an oil.

Workup

  1. additionA mixture of 15.0 g
  2. waitto stand at room temperature for 18 hours
  3. temperatureis heated
  4. temperatureat reflux temperature for one hour
  5. distillationthe solvent is distilled off
  6. extractionThe residue is extracted with methylenechloride
  7. washThe organic layer is washed with dilute hydrochloric acid and water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated to an oil
  10. customThe oil is triturated with a little methylene chloride
  11. filtrationthe insoluble material is filtered off
  12. concentrationThe mother liquor is concentrated

Sources & evidence

ORD record
ord-506292579fee4fdbad856e201694d068
Source dataset
uspto-grants-1981_09
Patent number
US04289769

Reaction notes

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