Ammonia → 4-(Chloromethyl)-2-(4-isopropylphenyl)-5-methyloxazole

HRID 748031Notes

Reaction equation

HRID 748031 reaction equation
[CH3:1][C:2]1[N+:3]([O-])=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[O:5][C:6]=1[CH3:7].P(Cl)(Cl)([Cl:20])=O.N>C(Cl)(Cl)Cl>[Cl:20][CH2:1][C:2]1[N:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[O:5][C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 59751022HCID 59751022, compound

Product 1

HCID 219742554-(Chloromethyl)-2-(4-isopropylphenyl)-5-methyloxazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

38 g of 4,5-Dimethyl-2-(4-(2-propyl)-phenyl)-oxazole 3-oxide are dissolved in 200 ml of chloroform, 16.4 ml of phosphorus oxychloride are added and the mixture is heated under reflux for 30 minutes. The reaction mixture is cooled to 0° C., a slightly alkaline pH is established using ammonia and the mixture is extracted three times with in each case 500 ml of ethyl acetate. The combined organic phases are washed with water and dried over MgSO4 and the solvent is then removed under reduced pressure. The residue is purified on silica gel using the mobile phase n-heptane:ethyl acetate=80:1=>5:1. This gives 10.3 g of 4-chloromethyl-5-methyl-2-(4-(2-propyl)-phenyl)-oxazole as a colorless solid. C14H16CINO (249.74), MS(ESI): 250 (M+H+).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 30 minutes
  3. extractionthe mixture is extracted three times with in each case 500 ml of ethyl acetate
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over MgSO4
  6. customthe solvent is then removed under reduced pressure
  7. customThe residue is purified on silica gel using the mobile phase n-heptane

Sources & evidence

ORD record
ord-ff2ae2ce6f9d40009fbc99005e4d801c
Source dataset
uspto-grants-2008_07
Patent number
US07399777B2

Reaction notes

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