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

HRID 490749Notes

Reaction equation

HRID 490749 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 column chromatography on silica gel yields 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-c29db1e74c7a48538010181563f09c67
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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