Diethylamine → N,N-diethyl-4-formylbenzamide

HRID 628596Notes

Reaction equation

HRID 628596 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.O=S(Cl)Cl.[NH:16]([CH2:19][CH3:20])[CH2:17][CH3:18]>>[CH2:17]([N:16]([CH2:19][CH3:20])[C:1](=[O:3])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)[CH3:18]

Participants

4

Reactant 3

HCID 8021DiethylamineHCID 120884-Formylbenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 10954698N,N-diethyl-4-formylbenzamideYield 90.3%

Procedure

4-Carboxybenzaldehyde (1.07 g, 7.13 mmol) was added into SOCl2 (5 ml). The mixture was refluxed for 6 hours until the solid was totally dissolved in solution. Then SOCl2 was evaporated under reduced pressure. Toluene (10 ml) was added to the residue and then removed under reduced pressure. The resulting residue was dissolved in anhydrous DCM (10 ml). Et2NH (20 mmol, 2.07 ml) was added dropwise. The solution was stirred at room temperature overnight. The solvent was removed under reduced pressure and the resulting residue was subjected to flash chromatography (EtOAc/Hexanes=30%˜50%) to give compound (1) (1.32 g, 6.44 mmol, yield 90%). 1H NMR (CDCl3) δ 10.06 (s, 1H), 7.95 (d, 2H), 7.55 (d, 2H), 3.58 (quart, 2H), 3.23 (quart, 2H), 1.28 (t, 3H), 1.13 (t, 3H).

Workup

  1. temperatureThe mixture was refluxed for 6 hours until the solid
  2. dissolutionwas totally dissolved in solution
  3. customThen SOCl2 was evaporated under reduced pressure
  4. additionToluene (10 ml) was added to the residue
  5. customremoved under reduced pressure
  6. dissolutionThe resulting residue was dissolved in anhydrous DCM (10 ml)
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9cd2158b244f44abb4a5cd99d307fa92
Source dataset
uspto-grants-2016_04
Patent number
US09314463B2

Reaction notes

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