Phosphorus oxychloride → 4-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole

HRID 2194294Notes

Reaction equation

HRID 2194294 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][C:7]1[N+:8]([O-])=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:10][C:11]=1[CH3:12]>C(Cl)(Cl)Cl>[Cl:3][CH2:6][C:7]1[N:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:10][C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 3236994HCID 3236994, compound

Product 1

HCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazoleYield 68%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

383 g of phosphorous oxychloride was slowly added dropwise into chloroform (2 L) solution of 430 g of 4,5-dimethyl-2-phenyloxazole N-oxide. After the dropwise addition, the solution was stirred for 2 hours at room temperature. The reaction mixture was concentrated in vacuo, and 2 L of ethyl acetate was added to the residue. The foregoing ethyl acetate solution was added to mixed solution of 2 L of ice water and 1.2 L of 25% sodium hydroxide solution under stirring. The liquid was separated, and the ethyl acetate layer was washed with 1 L of brine, and dried with 300 g of anhydrous sodium sulfate. After filtration in vacuo, the filtrate was concentrated. Ethanol:n-hexane=1:10 (1.1 L) was added to the crystalline residue, and then filtered off. The crystal was dried under reduced pressure at 40° C. for 1 hour, 321 g of the subject compound was prepared.

Workup

  1. additionAfter the dropwise addition
  2. concentrationThe reaction mixture was concentrated in vacuo, and 2 L of ethyl acetate
  3. additionwas added to the residue
  4. additionThe foregoing ethyl acetate solution was added
  5. additionto mixed solution of 2 L of ice water and 1.2 L of 25% sodium hydroxide solution
  6. stirringunder stirring
  7. customThe liquid was separated
  8. washthe ethyl acetate layer was washed with 1 L of brine
  9. dry with materialdried with 300 g of anhydrous sodium sulfate
  10. filtrationAfter filtration in vacuo
  11. concentrationthe filtrate was concentrated
  12. additionEthanol:n-hexane=1:10 (1.1 L) was added to the crystalline residue
  13. filtrationfiltered off
  14. customThe crystal was dried under reduced pressure at 40° C. for 1 hour

Sources & evidence

ORD record
ord-05745ea760da4e8d94b08d36c9251427
Source dataset
uspto-grants-2012_12
Patent number
US08329913B2

Reaction notes

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