反応 #9661

反応方程式

tert-butyl nitrite

2-amino-6-trifluoromethylbenzthiazole

hydrochloric acid

→

semi-solid

収率 92.0%

2-Chloro-6-(trifluoromethyl)-1,3-benzothiazole

収率 92.0%

溶媒

acetonitrile

acetonitrile

反応条件

後処理

1. 1
   その他In a three-necked flask fitted with a condenser
2. 2
   温度The mixture was heated at 65° C. for 30 minutes
3. 3
   温度cooled
4. 4
   抽出The mixture was extracted with ethyl acetate
5. 5
   その他The organic phase was separated
6. 6
   乾燥dried (MgSO4)
7. 7
   濃縮concentrated under reduced pressure

実験手順

In a three-necked flask fitted with a condenser, a suspension of copper II chloride (370 mg, 2.75 mmol) in acetonitrile (5 mL) was treated with tert-butyl nitrite (0.41 mL, 3.44 mmol) and stirred at rt for 10 minutes. A solution of 2-amino-6-trifluoromethylbenzthiazole (500 mg, 2.29 mmol) in acetonitrile (1 mL) was then added dropwise. The mixture was heated at 65° C. for 30 minutes, then cooled and diluted with an excess of 1 N aqueous hydrochloric acid solution. The mixture was extracted with ethyl acetate. The organic phase was separated, dried (MgSO4), and concentrated under reduced pressure. An orange semi-solid (501 mg, 92%) was obtained and used without further purification. 1H NMR (300 MHz, CDCl3) δ 8.10–8.05 (m, 2 H), 7.74 (d, 1 H); LC-MS m/z 238.2 (MH+), ret. time 3.76 min TLC Rf=0.50 (9:1 hexanes/ethyl acetate).

出典