反应 #80647

反应方程式

sodium acetate

hydroxylamine-O-sulfonic acid

2-methyl-3-[1-[4-[[2(trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl) -1H-imidazol-2-yl]pyridine

2-methyl-3-[1-[4-[[2-(trimethylsilyl) ethyl]sulfonyl]phenyl]-4-(trifluoromethyl) -1H-imidazol-2-yl]pyridine

n-Bu4NF

→

4-[2-(2-methylpyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide

收率 84.0%

溶剂

water

Water

ethyl acetate

THF

反应条件

后处理

1. 1
   温度The mixture was heated
2. 2
   温度to reflux for 1 hour
3. 3
   其他The organic phase was separated
4. 4
   洗涤washed with sat. NaHCO3 solution, water, and brine
5. 5
   干燥dried over MgSO4
6. 6
   过滤filtered
7. 7
   浓缩The filtrate was concentrated
8. 8
   其他the residue was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5)

实验过程

To a solution of 2-methyl-3-[1-[4-[[2(trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl) -1H-imidazol-2-yl]pyridine from Step 1 (0.234 g, 0.0005 mol) in 1.5 mL of dry THF was added n-Bu4NF (1.5 mL of 1.0M THF solution, 1.5 mmol). The mixture was heated to reflux for 1 hour and cooled to room temperature. A solution of sodium acetate (0.19 g, 2.3 mmol) in 3 mL of water and hydroxylamine-O-sulfonic acid (0.28 g, 2.5 mmol) were added sequentially and the mixture was stirred for 1 hour. Water (7 mL) and ethyl acetate (7 mL) were added. The organic phase was separated and washed with sat. NaHCO3 solution, water, and brine, dried over MgSO4 and filtered. The filtrate was concentrated and the residue was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5) to give 0.16 g of 4-[2-(2-methylpyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide as a colorless solid (84%): mp 235°-237° C. Anal. Calc'd. for C16H13F3N4O2S: C, 50.26; H, 3.43; N, 14.65; S, 8.39. Found: C, 50.06; H, 3.29; N, 14.44; S, 8.52.

来源