Hydrogen Peroxide → HCID 136105219, compound

HRID 2079228Notes

Reaction equation

HRID 2079228 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[NH:10][C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])#[N:2].[OH-:21].[Na+].OO>C(O)C>[CH3:19][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:11]1[NH:2][C:1](=[O:21])[C:3]2[C:4](=[CH:5][C:6]([CH3:9])=[CH:7][CH:8]=2)[N:10]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 59213237HCID 59213237, compound

Product 1

HCID 136105219HCID 136105219, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mechanically stirred suspension of N-(2-cyano-5-methylphenyl)-2-methoxybenzamide (180 g, 0.67 mol) in 1.8 L ethanol under an N2 atmosphere was added 6 N sodium hydroxide solution (310 g in 1.25 L water). To the above mixture, 30% hydrogen peroxide (350 mL, 3.64 mol) was slowly added. The solution was then slowly heated to 80° C. and maintained at this temperature for 4 h. The reaction mixture was concentrated under reduced pressure to remove ethanol, giving a suspension, which was quenched with ice-cold water (1.8 L) and acidified with acetic acid to pH 5-6 to give a solid residue. The solid was filtered and washed with water, then dissolved in 5.5 L CH2Cl2 and washed with water (2×18 L). The organic layer was dried over sodium sulfate, and the solvent was removed under reduced pressure to give a light yellow solid (100 g, 54%). mp 165-170° C.

Workup

  1. temperaturemaintained at this temperature for 4 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto remove ethanol
  4. customgiving a suspension, which
  5. customwas quenched with ice-cold water (1.8 L)
  6. customto give a solid residue
  7. filtrationThe solid was filtered
  8. washwashed with water
  9. dissolutiondissolved in 5.5 L CH2Cl2
  10. washwashed with water (2×18 L)
  11. dry with materialThe organic layer was dried over sodium sulfate
  12. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-00e1295432194ca2b0f984c5db3fc32c
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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