1-(1,2,4-Triazolyl) Ketoxime Ether Amide and Its Application
A technology of ketoxime ether amide and triazole base, which is applied in the field of new compounds and their preparation, and can solve the problems of no reports of herbicidal and insecticidal activities.
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Embodiment 1
[0033] Example 1 N-benzyl-2-[3,3-dimethyl-1-(1,2,4-triazol-1-yl)butyl-2-methyleneaminooxy]acetamide (4a ) preparation
[0034]
[0035] 2.16g (20.2mmol) benzylamine, 1.95g (14.1mmol) potassium carbonate, 1.73g (2.88mmol) PEG600, 20mL dichloromethane, N 2 For protection, 3.02 g (27.0 mmol) of chloroacetyl chloride was slowly added dropwise under ice bath conditions, and the dropwise addition was completed in 30 minutes, and the reaction was tracked by TLC for 6.9 hours. Rotary evaporation, washing with water, drying, and ethanol recrystallization gave 2.67 g of white solid 3a, yield 71.9%, m.p.88-90°C.
[0036] 0.92g (5.0mmol) compound 2, 0.86g (4.96mmol) N-benzyl-2-chloroacetamide, 0.15g (0.5mmol) tetrabutylammonium bromide (TBAB), 0.08g (0.05mmol) KI, 15 mL of toluene. 1.98g of 20% sodium hydroxide (9.9mmol) solution was slowly added dropwise, and the dropwise addition was completed within 10min, and the temperature was slowly raised to 60°C, and the reaction was comple...
Embodiment 2
[0037] Example 2 N-(3-methylphenyl)-2-[3,3-dimethyl-1-(1,2,4-triazol-1-yl)butyl-2-methyleneamine oxide The preparation of base] acetamide (4b)
[0038]
[0039] Prepare 3b according to Example 1, react for 3.9h, and obtain 2.32g white solid after recrystallization from ethanol, yield 62.7%, m.p.86~87°C; prepare compound 4b according to Example 1, react for 2.8h, yield 24.2% , m.p.101-102°C. 1 H NMR (CDCl 3 , 400Hz) δ: 1.14(s, 9H, 3×CH 3 ), 2.37 (s, 3H, CH 3 ), 2.27 (s, 3H, CH 3 ), 4.73 (s, 2H, CH 2 ), 5.09 (s, 2H, NOCH 2 ), 6.97 (d, J=7.6Hz, 1H, C 6 h 4 4-H), 7.25(t, J=8.4Hz, 1H, C 6 h 4 5-H), 7.37(d, J=8.4Hz, 1H, C 6 h 4 6-H), 7.47(s, 1H, C 6 h 4 2-H), 7.94(s, 1H, C 2 h 2 N 3 3-H), 8.23(s, 1H, C 2 h 2 N 3 5-H), 9.19 (s, 1H, CONH).
Embodiment 3
[0040] Example 3 N-(3,4-dimethylphenyl)-2-[3,3-dimethyl-1-(1,2,4-triazol-1-yl)butyl-2-ylidene Preparation of methylaminooxy]acetamide (4c)
[0041]
[0042] Prepare 3c according to Example 1, react for 1.5h, and obtain 2.75g off-white solid after ethanol recrystallization, yield 69.2%, m.p.94~96°C; prepare compound 4c according to Example 1, react for 1.4h, yield 49.5% , m.p.121-123°C. 1 H NMR (CDCl 3 , 400Hz) δ: 1.14(s, 9H, 3×CH 3 ), 2.24(s, 3H, CH 3 ), 2.27 (s, 3H, CH 3 ), 4.73 (s, 2H, CH 2 ), 5.09 (s, 2H, NOCH 2 ), 7.11 (d, J=7.6Hz, 1H, C 6 h 3 5-H), 7.30 (dd, J 1 =8.0Hz,J 2 = 2.4Hz, 1H, C 6 h 3 6-H), 7.40(s, 1H, C 6 h 3 2-H), 7.93(s, 1H, C 2 h 2 N 3 3-H), 8.20(s, 1H, C 2 h 2 N 3 5-H), 9.15 (s, 1H, CONH).
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