Hydrogen Peroxide → 4-(4-(2,3-dihydrobenzo(1,4)dioxin-6-yl)-5-pyridin-2-yl-1H-imidazol-2-yl)benzamide

HRID 991545Notes

Reaction equation

HRID 991545 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:12]=[C:13]([C:22]4[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=4)[NH:14][C:15]=3[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-:31].[K+].[K+].OO.S([O-])(O)=O.[Na+]>CO>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:12]=[C:13]([C:22]4[CH:23]=[CH:24][C:25]([C:26]([NH2:27])=[O:31])=[CH:28][CH:29]=4)[NH:14][C:15]=3[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 9929763HCID 9929763, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 64197534-(4-(2,3-dihydrobenzo(1,4)dioxin-6-yl)-5-pyridin-2-yl-1H-imidazol-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-[4-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-5-pyridin-2-yl-1H-imidazol-2-yl]benzonitrile (1 g) was dissolved in methanol (200 ml). Potassium carbonate was added (1 g) and the resulting suspension treated dropwise with an aqueous hydrogen peroxide solution (10 ml of 30% w/v solution) at 0° C. The suspension was stirred at room temperature for 18 hours then cautiously poured into saturated sodium hydrogen sulfite solution (200 ml) at 0° C. The mixture was tested for the presence of oxidant (starch-iodide test strips) before organic solvent removal by rotary evaporation under reduced pressure. The crude product was digested in ethyl acetate (200 ml). The ethyl acetate layer was dried (MgSO4) and evaporated to dryness under reduced pressure. The title compound was isolated by silica gel column chromatography (using a 1:9:190 ammonia:methanol:dichloromethane solution as eluent) as a beige solid (153 mg, 15%). 1H NMR (250 MHz, CDCl3) δ: 4.26 (4H, brs), 6.05 (1H, brs), 6.60 (1H, brs), 6.87 (1 H, brd, J=7. 7 Hz) 7.0-7.25 (3H, 7.53 (2H, d, J=3.7 Hz), 7.76 (2H, d, J=8.2 Hz), 7.95 (2H, d, J=8.2 Hz), 8.47 (1H, d, J=4.6 Hz); m/z (ESMS): 399 (MH+).

Workup

  1. customThe mixture was tested for the presence of oxidant (starch-iodide test strips) before organic solvent removal by rotary evaporation under reduced pressure
  2. dry with materialThe ethyl acetate layer was dried (MgSO4)
  3. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4fd8b154cb444ccc8b8f54aa4245c6b4
Source dataset
uspto-grants-2002_10
Patent number
US06465493B1

Reaction notes

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