Ammonium Hydroxide → 4-(Chloromethyl)-2,5-diphenyloxazole

HRID 1621159Notes

Reaction equation

HRID 1621159 reaction equation
[CH3:1][C:2]1[N+:3]([O-])=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.P(Cl)(Cl)([Cl:22])=O.[NH4+].[OH-]>C(Cl)(Cl)Cl>[Cl:22][CH2:1][C:2]1[N:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 11807110HCID 11807110, compound

Product 1

HCID 109235994-(Chloromethyl)-2,5-diphenyloxazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
65 °C

Procedure

To a solution of 4-methyl-2,5-diphenyloxazole 3-oxide (395 mg, 1.57 mmol) in chloroform (2 mL) was added dropwise a solution of phosphorus oxychloride (265 mg, 161 μL, 1.73 mmol) in chloroform (2.00 mL) over a period of 10 min. The reaction mixture was stirred at 65° C. for 4 h and cooled to 0-5° C. At that temperature, NH4OH (25% aqueous solution, 10 mL) was added dropwise and the mixture was extracted with dichloromethane (3×40 mL). The combined organic phase was dried over MgSO4, filtered and concentrated in vacuo. The product was obtained after purification by flash chromatography (using silica gel and a dichloromethane/heptane gradient) as colorless solid (249 mg, 923 μmol, 58.7%).

Workup

  1. temperaturecooled to 0-5° C
  2. extractionthe mixture was extracted with dichloromethane (3×40 mL)
  3. dry with materialThe combined organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was obtained
  7. customafter purification by flash chromatography (

Sources & evidence

ORD record
ord-c7b88f2d41e94333bc19894d758bbae6
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

Loading…