Dimethylformamide → HCID 85746031, compound

HRID 1048609Notes

Reaction equation

HRID 1048609 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[NH:11][N:10]=[N:9]1.[CH3:14]N(C)C=O.[H-].[Na+].CI>O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[N:11]([CH3:14])[N:10]=[N:9]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1361865751-(2-Methylphenyl)-1,2-dihydro-5H-tetrazol-5-one

Product 1

HCID 85746031HCID 85746031, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of the above-mentioned 1-(2-methylphenyl)-1,4-dihydrotetrazole-5-one 69.8 g and N,N-dimethylformamide 380 mL was added 55% sodium hydride 18.2 g under ice-cooling. After stirring the resulting mixture for twenty minutes, thereto was added methyl iodide 59.4 g. The mixtures were raised to room temperature and were stirred for two and a half hours. To the reaction mixtures was added water and the mixtures were extracted with methyl tert-butyl ether. 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-methylphenyl)-4-methyl-1,4-dihydrotetrazole-5-one 52.5 g.

Workup

  1. temperaturecooling
  2. stirringwere stirred for two and a half hours
  3. customTo the reaction mixtures
  4. extractionthe mixtures were extracted with methyl tert-butyl ether
  5. washThe organic layers were washed with 10% hydrochloric acid, water and saturated saline
  6. dry with materialwere dried over anhydrous magnesium sulfate
  7. concentrationwere then concentrated under reduced pressure

Sources & evidence

ORD record
ord-1f9279bb168743e3b97e959e4aadcaee
Source dataset
uspto-grants-2016_07
Patent number
US09380782B2

Reaction notes

Loading…