Dimethylformamide → 1-(2-Methyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one

HRID 1048620Notes

Reaction equation

HRID 1048620 reaction equation
[CH3:1][C:2]1[C:7]([Br:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[NH:12][N:11]=[N:10]1.[CH3:15]N(C)C=O.[H-].[Na+].CI>O>[CH3:1][C:2]1[C:7]([Br:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[N:12]([CH3:15])[N:11]=[N:10]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1366461861-(2-Methyl-3-bromophenyl)-1,4-dihydrotetrazol-5-one

Product 1

HCID 898758451-(2-Methyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of the above-mentioned 1-(2-methyl-3-bromophenyl)-1,4-dihydrotetrazole-5-one 31.40 g and N,N-dimethylformamide 250 mL was added 60% sodium hydride 5.90 g under ice-cooling. The mixtures were raised to room temperature and were stirred for one hour. To the reaction mixtures was added methyl iodide 8.4 mL under ice-cooling. The mixtures were raised to room temperature and were stirred for fourteen hours. To the reaction mixtures was added water and the mixtures were extracted with ethyl acetate. The organic layers were washed with 10% hydrochloric acid, water and saturated saline, and were dried over anhydrous magnesium sulfate and were then concentrated under reduced pressure. The resulting residues were subjected to a silica gel column chromatography to give 1-(2-methyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter, referred to as “Intermediate (PRB-P)”) 8.47 g.

Workup

  1. temperaturecooling
  2. customTo the reaction mixtures
  3. temperaturecooling
  4. temperatureThe mixtures were raised to room temperature
  5. stirringwere stirred for fourteen hours
  6. customTo the reaction mixtures
  7. extractionthe mixtures were extracted with ethyl acetate
  8. washThe organic layers were washed with 10% hydrochloric acid, water and saturated saline
  9. dry with materialwere dried over anhydrous magnesium sulfate
  10. concentrationwere then concentrated under reduced pressure

Sources & evidence

ORD record
ord-f5bef391de834195a78ed3e7ffb0cc9f
Source dataset
uspto-grants-2016_07
Patent number
US09380782B2

Reaction notes

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