Water → 3-(Azidomethyl)-5-(trifluoromethyl)isoxazole

HRID 1025974Notes

Reaction equation

HRID 1025974 reaction equation
CS(O[CH2:6][C:7]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[O:9][N:8]=1)(=O)=O.[N-:16]=[N+:17]=[N-:18].[Na+].O>CN(C=O)C>[N:16]([CH2:6][C:7]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[O:9][N:8]=1)=[N+:17]=[N-:18]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86663141(5-(Trifluoromethyl)isoxazol-3-yl)methyl methanesulfonate

Product 1

HCID 866631403-(Azidomethyl)-5-(trifluoromethyl)isoxazoleYield 91.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8.7 g (5-(trifluoromethyl)isoxazol-3-yl)methyl methanesulfonate in 87 mL DMF was added 9.23 g sodium azide. The reaction mixture was stirred 3 h at RT. 80 mL water was added under cooling. The mixture was extracted with diethyl ether (3×100 mL) and the organic layers were washed with water (3×100 mL) and then with sat. NaCl solution (1×100 mL). The combined organic layer was dried over Na2SO4, filtered off and concentrated in vacuo to yield 6.26 g of the title compound as a brown oil.

Workup

  1. temperatureunder cooling
  2. extractionThe mixture was extracted with diethyl ether (3×100 mL)
  3. washthe organic layers were washed with water (3×100 mL)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered off
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-922f1767935b4225a5d543e9285cf157
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

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