Dimethylformamide → N,N-diethyl-4-formylbenzamide

HRID 929630Notes

Reaction equation

HRID 929630 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([OH:3])=O.CN(C)C=O.S(Cl)(Cl)=O.[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22]>ClCCl.C(O)C>[CH:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1]([N:23]([CH2:24][CH3:25])[CH2:21][CH3:22])=[O:3])=[CH:5][CH:6]=1)=[O:9]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8021DiethylamineHCID 120884-Formylbenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 10954698N,N-diethyl-4-formylbenzamideYield 32.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-carboxybenzaldehyde (100 g, 0.66 mol), 1 L of dimethylformamide and 2 L of dichloromethane was cooled in an ice bath. Thionyl chloride (53 mL, 0.73 mol) was added dropwise while stirring. After 18 hours at room temperature, the mixture was cooled again and diethylamine (275 mL, 2.6 mol) was added dropwise. After stirring at room temperature for one hour the solvent was evaporated, and the residue was dissolved in aqueous 0.1 M sodium hydroxide and extracted with ethyl acetate. The organic layers were washed with water and brine, dried over sodium sulfate and evaporated to give a yellow oil. Chromatography on silica gel with ethanol (0-2%) in dichloromethane gave 44.2 g (32%) of 4-formyl-N,N-diethylbenzamide as a yellow oil.

Workup

  1. temperaturewas cooled in an ice bath
  2. temperaturethe mixture was cooled again
  3. stirringAfter stirring at room temperature for one hour the solvent
  4. customwas evaporated
  5. dissolutionthe residue was dissolved in aqueous 0.1 M sodium hydroxide
  6. extractionextracted with ethyl acetate
  7. washThe organic layers were washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customto give a yellow oil

Sources & evidence

ORD record
ord-30c67606e15647c4a0d243b3e2837819
Source dataset
uspto-grants-2016_03
Patent number
US09296707B2

Reaction notes

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