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

HRID 2197955Notes

Reaction equation

HRID 2197955 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-de65a4b1c2c547958e0ac70671a26e98
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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