Reaktion #589218

Reaktionsgleichung

Oxalyl chloride

3-nitro-4-methylbenzoic acid

→

N-(3,4-dichlorobenzyl)-4-methyl-3-nitrobenzamide

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was evaporated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in methylene chloride (100 ml)
3. 3
   workup.ADDITION3,4-Dichlorobenzylamine (7.04 g), 4-dimethylaminopyridine (0.31 g) and triethylamine (13.9 ml) were added
4. 4
   workup.STIRRINGthe reaction mixture was stirred at ambient temperature for 16 hours
5. 5
   WaschenThe mixture was washed with a saturated aqueous sodium bicarbonate solution
6. 6
   Trocknendried over magnesium sulphate
7. 7
   Sonstigeevaporated The residue
8. 8
   Sonstigewas purified by column chromatography
9. 9
   workup.ADDITIONa 250:8:1 mixture of methylene chloride, methanol

Vorschrift

Oxalyl chloride (4.8 ml) was added to a solution of 3-nitro-4-methylbenzoic acid (9.06 g) in methylene chloride (100 ml) and DMF (a few drops) and the reaction stirred at ambient temperature for 16 hours. The reaction mixture was evaporated and the residue was dissolved in methylene chloride (100 ml). 3,4-Dichlorobenzylamine (7.04 g), 4-dimethylaminopyridine (0.31 g) and triethylamine (13.9 ml) were added and the reaction mixture was stirred at ambient temperature for 16 hours. The mixture was washed with a saturated aqueous sodium bicarbonate solution, dried over magnesium sulphate and evaporated The residue was purified by column chromatography using a 250:8:1 mixture of methylene chloride, methanol and a saturated aqueous ammonium chloride solution as eluent to give N-(3,4-dichlorobenzyl)-4-methyl-3-nitrobenzamide as a solid (9.95 g); NMR Spectrum: (DMSOd6) 2.57 (s, 3H), 4.47 (d, 2H), 7.31 (m, 1H), 7.56 (m, 2H), 7.61 (d, 1H), 8.1 (m, 1H), 8.47 (d, 1H), 9.3 (t, 1H).

Quelle