Hydrogen Peroxide → HCID 178491589, compound

HRID 1870340Notes

Reaction equation

HRID 1870340 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:25])[C:7]=1[NH:8][C:9](=[O:24])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:11]=1.[OH:26]O.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:26])[CH:5]=[C:6]([Cl:25])[C:7]=1[NH:8][C:9](=[O:24])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:11]=1

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 14798Sodium HydroxideHCID 154575Piclamilast

Product 1

HCID 178491589HCID 178491589, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

A stirred suspension of N-(3,5-dichloropyrid-4yl)-3-cyclopentyloxy-4-methoxybenzamide (2.0 g; that is prepared as described in Example 6) in glacial acetic acid (8 mL) is treated with an aqueous solution of hydrogen peroxide (6 mL; 27.5%). The mixture is stirred for 3 hours at 70-80° C. and then it is treated with a further portion of hydrogen peroxide solution (4 mL), and the solution is stirred for a further 12 hours. The solution is then cooled, basified by treatment with concentrated aqueous sodium hydroxide solution, and extracted with dichloromethane (2×30 mL). The organic extract is washed with brine (30 mL), dried over magnesium sulfate and evaporated. The resulting residue recrystallized from ethyl acetate, to give 3,5-dichloro-4-(3-cyclopentyloxy-4-methoxybenzamido)pyridine-N-oxide (0.73 g), m.p. 118-120° C. [Elemental analysis: C,53.0; H,4.4; N,6.8%; calculated for C18H18O4N2Cl2 :0.5H2O: C,53.2; H 4.7; N 6.9%].

Workup

  1. customthat is prepared
  2. stirringthe solution is stirred for a further 12 hours
  3. temperatureThe solution is then cooled
  4. extractionextracted with dichloromethane (2×30 mL)
  5. extractionThe organic extract
  6. washis washed with brine (30 mL)
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe resulting residue recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-828e6bb0aee24c6e9275910006079d46
Source dataset
uspto-grants-2000_08
Patent number
US06096768

Reaction notes

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