Reaction #1135819

ord-413944e88aa3430ea8aa7ef4a07e26e8

Reaction equation

O=C([O-])O.[Na+]
sodium bicarbonate
Cc1c(-n2nn[nH]c2=O)cccc1C(F)(F)F
1-(2-methyl-3-trifluoromethylphenyl)-1,4-dihydrotetrazole-5-one
O=C([O-])[O-].[K+].[K+]
potassium carbonate
COS(=O)(=O)OC
dimethyl sulfate
Cc1c(-n2nnn(C)c2=O)cccc1C(F)(F)F
1-(2-methyl-3-trifluoromethylphenyl)-4-methyl-1,4-dihydrotetrazole-5-one

Conditions

Temperature
25°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherTo the reaction mixtures
  2. 2
    Extractionthe mixtures were extracted with ethyl acetate
  3. 3
    WashThe organic layers were washed with aqueous saturated sodium bicarbonate solution
  4. 4
    Dryingwere dried over anhydrous sodium sulfate
  5. 5
    ConcentrationThe resulting mixtures were concentrated under reduced pressure

Procedure

A mixture of 1-(2-methyl-3-trifluoromethylphenyl)-1,4-dihydrotetrazole-5-one, potassium carbonate 11.20 g, dimethyl sulfate 3.71 g and N,N-dimethylformamide 150 mL was stirred at 25° C. for one hour. To the reaction mixtures was added aqueous saturated sodium bicarbonate solution and the mixtures were extracted with ethyl acetate. The organic layers were washed with aqueous saturated sodium bicarbonate solution and were dried over anhydrous sodium sulfate. The resulting mixtures were concentrated under reduced pressure to give 1-(2-methyl-3-trifluoromethylphenyl)-4-methyl-1,4-dihydrotetrazole-5-one 5.13 g.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09380782B2uspto-grants-2016_07