Reaction equation
C([Li])CCC.[CH3:6][N:7]1[C:11]([CH3:12])=[N:10][N:9]=[N:8]1.O1CCCC1.[F:18][C:19]1[CH:28]=[CH:27][C:22]([C:23](OC)=[O:24])=[C:21]([NH:29][CH3:30])[CH:20]=1>CCCCCC.O>[F:18][C:19]1[CH:28]=[CH:27][C:22]([C:23](=[O:24])[CH2:12][C:11]2[N:7]([CH3:6])[N:8]=[N:9][N:10]=2)=[C:21]([NH:29][CH3:30])[CH:20]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of butyl lithium in hexane (50 ml of 1.6M solution) was added slowly to a stirred mixture of 1,5-dimethyltetrazole (7.84 g) and dry tetrahydrofuran (170 ml) at 0°-5° under nitrogen. The mixture was stirred at 0°-5° for 0.5 hour and then methyl 4-fluoro-2-methylaminobenzoate (4.84 g) was added in portions at 0°-5°. The mixture was stirred at room temperature for 3 hours and then poured into water (500 ml). The resulting mixture was extracted with dichloromethane (5×60 ml). The extract was dried and evaporated to give an oil which partially solidified overnight. The solid was collected by filtration, washed with toluene and dried in vacuo to give the novel compound 1-(4-fluoro-2-methylaminophenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethanone, m.p. 132°-134°.
Workup
- stirringThe mixture was stirred at room temperature for 3 hours
- extractionThe resulting mixture was extracted with dichloromethane (5×60 ml)
- customThe extract was dried
- customevaporated
- customto give an oil which partially solidified overnight
- filtrationThe solid was collected by filtration
- washwashed with toluene
- customdried in vacuo
Sources & evidence
- ORD record
- ord-7340d66b0e6e414fb721ae3a56ac4fc4
- Source dataset
- uspto-grants-1987_04
- Patent number
- US04659718
Linked notes
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