Dimethylamine → 4-formyl-N,N-dimethylbenzamide

HRID 907911Notes

Reaction equation

HRID 907911 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1)=[O:2].S(Cl)(Cl)=O.[CH3:16][NH:17][CH3:18].O>C(Cl)Cl.CN(C=O)C>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:17]([CH3:18])[CH3:16])=[O:8])=[CH:5][CH:4]=1)=[O:2]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 120884-Formylbenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 105592054-formyl-N,N-dimethylbenzamideYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-formylbenzoic acid (4.00 g, 26.7 mmol) in dry DCM (8 mL) were added thionyl chloride (2.92 g, 40.0 mmol) and DMF (0.6 mL) dropwise at ambient temperature under nitrogen. The reaction mixture was refluxed for 2 h. After cooling, this mixture was added to 33% dimethylamine in water (10.5 mL, 72 mmol) dropwise over 15 min in an ice-water bath, and the reaction mixture stirred for 1 h at the same temperature. The solvent was evaporated in vacuums. The residue was purified by chromatography on silica gel to give the title compound (2.5 g, yield 53%) as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 2.86 (s, 3H), 3.30 (s, 3H), 7.60 (d, J=7.6 Hz, 2H), 7.95 (d, J=7.6 Hz, 2H), 10.04 (s, 1H); LC-MS (ESI) m/z: 178 (M+1)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. temperatureAfter cooling
  3. customThe solvent was evaporated in vacuums
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-014c3f63cea24c4b9e04c770876e92e0
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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