反応 #442916

反応方程式

5-Bromo-2-thiophenecarboxylic acid

triethylamine

4-methoxy-3-(4-methyl-1-piperazinyl)benzenamine

→

title compound

5-Bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]thiophene-2-carboxamide

溶媒

thionyl chloride

反応条件

後処理

1. 1
   温度cooled
2. 2
   その他evaporated in vacuo
3. 3
   その他the residue azeotroped with toluene
4. 4
   workup.DISSOLUTIONThe residue was redissolved in CH2Cl2 (10 ml)
5. 5
   その他evaporated in vacuo
6. 6
   その他partitioned
7. 7
   乾燥dried over Na2SO4
8. 8
   ろ過filtered
9. 9
   その他the filtrate evaporated in vacuo to a brown gum
10. 10
    その他The gum was purified by flash silica-gel chromatography
11. 11
    洗浄eluted with 3%MeOH/CHCl3

実験手順

5-Bromo-2-thiophenecarboxylic acid (0.375;1.8 mmol) was heated at reflux in thionyl chloride (8 ml) for 30 minutes, cooled, evaporated in vacuo and the residue azeotroped with toluene. The residue was redissolved in CH2Cl2 (10 ml) and treated with dry triethylamine (0.25 ml;1.81 mmol) and 4-methoxy-3-(4-methyl-1-piperazinyl)benzenamine (0.4 g;1.81 mmol). The solution was stirred under Ar (18 hours), evaporated in vacuo and partitioned satd. K2CO3 (aq)/EtOAc. The organic phases were combined, dried over Na2SO4, filtered and the filtrate evaporated in vacuo to a brown gum. The gum was purified by flash silica-gel chromatography and eluted with 3%MeOH/CHCl3 to yield the title compound as a brown gum which crystallised on standing (0.388 g;52%), and was converted to the oxalate salt, mp=114°-115° C.

出典