Methyl iodide → 3-Benzyl-4-(2,2-diethoxyethyl)-5-methylthio-1,2,4-triazole
Reaction equation
[Na].[CH2:2]([C:9]1[N:13]([CH2:14][CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[C:12](=[S:22])[NH:11][N:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:23]I>CO>[CH2:2]([C:9]1[N:13]([CH2:14][CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[C:12]([S:22][CH3:23])=[N:11][N:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In 1 l of methanol was dissolved 11.0 g of sodium, followed by the addition of 134.4 g of 3-benzyl-4-(2,2-diethoxyethyl)-4H-1,2,4-triazole-5-thione. Then, 30.0 ml of methyl iodide was added dropwise and the mixture was stirred for 20 minutes. Thereafter, the reaction mixture was treated as in Reference Example 3 to obtain 140 g of 3-benzyl-4-(2,2-diethoxyethyl)-5-methylthio-1,2,4-triazole as an oil. This oil was gradually added to 430 ml of concentrated sulfuric acid previously cooled with ice-sodium chloride and, then at room temperature, the mixture was stirred for 30 minutes, after which it was poured into 5 l of ice-water. The mixture was neutralized with concentrated aqueous ammonia and the resultant crystals were collected by filtration. The crystalline 3-methylthio-11H-s-triazolo[3,4-b][3]benzazepine thus obtained was recrystallized from methanol. This procedure yielded colorless needles melting at 168°-169° C. Infrared absorption spectrum of this product was identical with that of the product obtained in Example 1.
Workup
- additionThereafter, the reaction mixture was treated as in Reference Example 3
Sources & evidence
- ORD record
- ord-ec8ad1191f3a4176a50ad6485ef20b80
- Source dataset
- uspto-grants-1979_04
- Patent number
- US04150139
Reaction notes
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