反応 #2195520

反応方程式

HCl

4-bromo-2-(2H-[1,2,4]triazol-3-yl)-phenylamine

chloroacetyl chloride

NaOH

→

title compound

収率 46.0%

9-Bromo-6H-1,3,3a,6-tetraaza-benzo[e]azulen-5-one

収率 46.0%

溶媒

dioxane

pyridine

diethylether

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred for 17.5 h at ambient temperature
2. 2
   workup.ADDITIONThe pH thereby dropped to about pH=9 and it
3. 3
   その他After evaporation the residue
4. 4
   workup.STIRRINGwas stirred at 15° C. for 30 min in water (650 mL)
5. 5
   ろ過The crystals were filtered off
6. 6
   洗浄washed with cold water
7. 7
   その他dried in vacuo

実験手順

A solution of 4-bromo-2-(2H-[1,2,4]triazol-3-yl)-phenylamine (25.0 g, 105 mmol) in dioxane (870 mL) and pyridine (10.0 mL) was cooled to 12° C. A solution of chloroacetyl chloride (9.56 mL, 121 mmol) in diethylether (34.7 mL) was added dropwise over a period of 8 min. The mixture was stirred at 10-12° C. for 75 min and treated within 5 min with aq NaOH 2N (126 mL, 251 mmol). The mixture was stirred for 17.5 h at ambient temperature. The pH thereby dropped to about pH=9 and it was adjusted to pH=8 with 3N HCl (6 mL). After evaporation the residue was stirred at 15° C. for 30 min in water (650 mL) and ethyl acetate (22 mL). The crystals were filtered off, washed with cold water and dried in vacuo. Trituration in ethyl acetate (100 mL) afforded the title compound (13.4 g, 46%) as a light yellow solid. MS: m/e=279.0/281.0 (M+H+).

出典