Sodium Azide → 4-Azidomethyl-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazole

HRID 860627Notes

Reaction equation

HRID 860627 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[N-:19]=[N+:20]=[N-:21].[Na+]>CO.O>[N:19]([CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8])=[N+:20]=[N-:21]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 102363332-(4-Trifluoromethylphenyl)-4-chloromethyl-5-methyloxazole

Product 1

HCID 587657284-Azidomethyl-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazoleYield 85.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-chloromethyl-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazole (2.4 g, 8.71 mmol) in methanol (13 mL) is added sodium azide (1.13 g, 17.4 mmol) in water (10 mL). The mixture is heated to reflux for 3 hrs, cooled to room temperature, majority of the methanol is evaporated, the residue is extracted with ethyl acetate, dried, concentrated and colun chromatography on silica gel gave the title compound (2.10 g).

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 3 hrs
  3. custommajority of the methanol is evaporated
  4. extractionthe residue is extracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a8b0d5a0a98e4a778e140b4cbd9b0279
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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