Dimethylformamide → 1-(2-Methyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one
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]1Participants
Procedure
To a mixture of 1-(2-methyl-3-bromophenyl)-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 9) 31.40 g and N,N-dimethylformamide 250 ml was added 60% sodium hydride 5.90 g under ice-cooling. The reaction mixture was raised to room temperature and was stirred for one hour. To the reaction mixture was added methyl iodide 8.4 ml under ice-cooling. The resulting mixture was raised to room temperature and was stirred for fourteen hours. To the reaction mixture was added water and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with 10% hydrochloric acid, water and saturated saline, and was dried over anhydrous magnesium sulfate and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-methyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one 8.47 g.
Workup
- temperaturecooling
- temperaturecooling
- temperatureThe resulting mixture was raised to room temperature
- stirringwas stirred for fourteen hours
- extractionthe reaction mixture was extracted with ethyl acetate
- washThe organic layer was washed with 10% hydrochloric acid, water and saturated saline
- dry with materialwas dried over anhydrous magnesium sulfate
- concentrationwas then concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-cc6b3a3578ee4d12aef6e7c57a2680f8
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09314023B2
Reaction notes
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