Diethylamine → N,N-diethyl-4-formylbenzamide

HRID 2174265Notes

Reaction equation

HRID 2174265 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-85d8a1f1da9d4f0d86eb8c0a2fa05370
Source dataset
uspto-grants-2015_06
Patent number
US09061026B2

Reaction notes

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