Water → 2-Methoxy-N-(2-pyridinylmethyl)-N-[4-(tetradecyloxy)benzoyl]benzamide

HRID 247916

Reaction equation

HRID 247916 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9](=[O:31])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:12][CH:11]=1.[C:32](Cl)(=[O:41])[C:33]1[C:34]([O:39][CH3:40])=[CH:35][CH:36]=[CH:37][CH:38]=1.O>O1CCCC1.[H-].[Na+]>[CH3:40][O:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[C:32]([N:8]([CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:9](=[O:31])[C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:14][CH:15]=1)=[O:41]

Participants

6

Reactant 3

HCID 962WaterHCID 889692-Methoxybenzoyl chlorideHCID 10093859N-(2-Pyridinylmethyl)-4-(tetradecyloxy)benzamide

Product 1

HCID 190164342-Methoxy-N-(2-pyridinylmethyl)-N-[4-(tetradecyloxy)benzoyl]benzamideYield 96.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24758Sodium hydrideSolvent

Procedure

To a solution of 1 g of product from Example 4 in 15 ml of dry tetrahydrofuran is added in one portion 0.0622 g of sodium hydride. The mixture is heated at reflux temperature for 2 hours, cooled to room temperature and 0.442 g o-anisoyl chloride is added. The reaction is then heated at reflux for 1.5 hours, cooled to room temperature, poured into water and extracted with ethyl acetate. The organic layer is washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel: 35% ethyl acetate/hexane) to give 1.27 g of the desired product.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux temperature for 2 hours
  3. temperatureThe reaction is then heated
  4. temperatureat reflux for 1.5 hours
  5. temperaturecooled to room temperature
  6. extractionextracted with ethyl acetate
  7. washThe organic layer is washed with saturated sodium chloride
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by column chromatography (silica gel: 35% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ab919752fb384c5da7e745d191f91429
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Linked notes

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