Hydrogen Peroxide → HCID 136105219, compound

HRID 2406163Notes

Reaction equation

HRID 2406163 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%). mp165-170° C. 1H NMR (CDCl3) δ 2.429 (s, 3H), 4.2 (s, 3), 6.8-7.2 (m, 3H), 7.4-7.6 (m, 2H), 8.2-8.4 (d, 1H), 8.6 (s, 1H), 10.8 (bs, 1H) ppm; 13C NMR (CDCl3) δ 21.68, 55.6, 111.3, 118.2, 119.6, 121.1, 125.7, 127.14, 127.64, 130.96, 132.56, 144.9, 149.06, 150.42, 157.25, 161.52. M/z (obs., [m+H]+)=268.

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-b5a39df401cb43d3ab5dccd8ff99277b
Source dataset
uspto-grants-2014_08
Patent number
US08809353B2

Reaction notes

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