Potassium Carbonate → N-[4-(3-Chloro-5-nitro-phenoxymethyl)-phenyl]-acetamide

HRID 2358790Notes

Reaction equation

HRID 2358790 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[CH:3]=1.[OH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1)[O:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 330981-Chloro-3,5-dinitrobenzeneHCID 1521414-Acetaminobenzyl alcohol

Product 1

HCID 68456880N-[4-(3-Chloro-5-nitro-phenoxymethyl)-phenyl]-acetamideYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product from Example 193a (1.00 g, 4.9 mmol), and the product from Example 197b (0.90 g, 5.4 mmol) and K2CO3 (0.86 g, 6.2 mmol) in DMF (20 mL) were heated at 100° C. for 10 hours. The reaction mixture was cooled to room temperature, diluted with H2O. The resulting solid was collected by filtration, washed with H2O, and dried in vacuum to give brown crystal, which was purified by silica gel column chromatography eluting with 5:2 EtOAc/hexane to give the title compound as a dark orange crystal (0.47 g, 30%).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with H2O
  3. customdried in vacuum
  4. customto give brown crystal, which
  5. customwas purified by silica gel column chromatography
  6. washeluting with 5:2 EtOAc/hexane

Sources & evidence

ORD record
ord-aebad77e37154c228549d344c213d3f9
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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