Hydrogen Peroxide → HCID 71227215, compound

HRID 2409912Notes

Reaction equation

HRID 2409912 reaction equation
OO.[Cl:3][C:4]1[O:5][C:6]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])=[CH:7][N:8]=1.C([O-])([O-])=[O:18].[K+].[K+]>CS(C)=O>[Cl:3][C:4]1[O:5][C:6]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]([NH2:13])=[O:18])=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 71226687HCID 71226687, compound

Product 1

HCID 71227215HCID 71227215, compoundYield 111.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

30% H2O2 (28.7 mL, 281.0 mmol) was slowly added to a 0° C. mixture of 3-(2-chlorooxazol-5-yl)benzonitrile (8.20 gm, 40.10 mmol) and K2CO3 (3.88 gm, 28.10 mmol) in DMSO (75 mL). The ice bath was removed and the reaction mixture was stirred at rt. After 24 h the reaction mixture was partitioned between EtOAc and water. The organic phase was isolated, washed with saturated aqueous NaCl (2×), dried over MgSO4, filtered and concentrated to give the product, 3-(2-chlorooxazol-5-yl)benzamide, (7.00 gm, 31.40 mmol, 78% yield) as a light yellow solid. Anal. Calcd. for C10H7ClN2O2 m/z 222.0, found: 223.0 (M+H)+. Crude product was used without purification.

Workup

  1. customThe ice bath was removed
  2. customAfter 24 h the reaction mixture was partitioned between EtOAc and water
  3. customThe organic phase was isolated
  4. washwashed with saturated aqueous NaCl (2×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-59b84206aab34ab48783649617887743
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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