Dimethyl Sulfate → 1-(2-Methyl-3-trifluoromethylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one

HRID 1048637Notes

Reaction equation

[CH3:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N:12]1[C:16](=[O:17])[NH:15][N:14]=[N:13]1.[C:18](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][CH:5]=[CH:4][C:3]=1[N:12]1[C:16](=[O:17])[N:15]([CH3:18])[N:14]=[N:13]1

Participants

Conditions

Temperature: 25 °C

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.

Workup

customTo the reaction mixtures
extractionthe mixtures were extracted with ethyl acetate
washThe organic layers were washed with aqueous saturated sodium bicarbonate solution
dry with materialwere dried over anhydrous sodium sulfate
concentrationThe resulting mixtures were concentrated under reduced pressure

Sources & evidence

ORD record: ord-413944e88aa3430ea8aa7ef4a07e26e8
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09380782B2

Reaction notes

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