Potassium Carbonate → HCID 21699281, compound

HRID 1597254Notes

Reaction equation

HRID 1597254 reaction equation
[OH:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1.C1(C)C=CC(S(O[CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:12][O:11][C:10]1[C:2]([O:1][CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)=[CH:3][C:4]([N+:13]([O-:15])=[O:14])=[C:5]([CH:9]=1)[C:6]([NH2:8])=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21699258HCID 21699258, compoundHCID 86757430HCID 86757430, compound

Product 1

HCID 21699281HCID 21699281, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Hydroxy-5-methoxy-2-nitrobenzamide (1.86 g, 9.5 mmol) and 2-(4-pyridyloxy)ethyl paratoluene sulphonate (3.3 g, 11.2 mmol) were mixed in the presence of potassium carbonate (1.7 g, 12.3 mmol) and anhydrous DMF (25 ml) and heated at 80° C. for 2 hours. The reaction mixture was allowed to cool overnight, the DMF was removed by evaporation and the residue was quenched into water (250 ml). The solid was collected by filtration and washed with a mixture of acetone/ether (1/1) to give 5-methoxy-2-nitro-4-(2-(4-pyridyloxy)ethoxy)benzamide as a cream solid (2.16 g, 68%).

Workup

  1. temperatureto cool overnight
  2. customthe DMF was removed by evaporation
  3. customthe residue was quenched into water (250 ml)
  4. filtrationThe solid was collected by filtration
  5. washwashed with a mixture of acetone/ether (1/1)

Sources & evidence

ORD record
ord-5255c1a249a14928aba1188759abb3d8
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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