Ammonia → 4-Chloromethyl-5-phenyl-2-p-tolyloxazole

HRID 253338

Reaction equation

HRID 253338 reaction equation
[CH3:1][C:2]1[N+:3]([O-])=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[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:23])=O.N>C(Cl)(Cl)Cl>[Cl:23][CH2:1][C:2]1[N:3]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[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 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 589341914-Methyl-5-phenyl-2-p-tolyloxazole 3-oxide

Product 1

HCID 574345034-Chloromethyl-5-phenyl-2-p-tolyloxazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

6.4 g of 4-methyl-5-phenyl-2-p-tolyloxazole 3-oxide are dissolved in 50 ml of chloroform, 2.4 ml of phosphorus oxychloride are added and the mixture is, under reflux, heated at the boil for 30 minutes. The reaction mixture is cooled to 0° C., the pH is made slightly alkaline using ammonia and the mixture is extracted three times with in each case 100 ml of ethyl acetate. The combined organic phases are washed with water and dried over MgSO4, and the solvent then removed under reduced pressure. This gives 5.4 g of 4-chloromethyl-5-phenyl-2-p-tolyloxazole as a yellow solid. C17H14ClNO (283.76), MS (ESI)=284 (M+H+), Rf (n-heptane:ethyl acetate)=7:1)=0.41.

Workup

  1. temperatureunder reflux
  2. temperatureheated at the boil for 30 minutes
  3. extractionthe mixture is extracted three times with in each case 100 ml of ethyl acetate
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over MgSO4
  6. customthe solvent then removed under reduced pressure

Sources & evidence

ORD record
ord-d4490a45948440848b18fbd1b862f094
Source dataset
uspto-grants-2011_01
Patent number
US07872034B2

Linked notes

Loading…