반응 #442916

반응 방정식

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

용매

thionyl chloride

반응 조건

후처리

1. 1
   온도cooled
2. 2
   기타evaporated in vacuo
3. 3
   기타the residue azeotroped with toluene
4. 4
   workup.DISSOLUTIONThe residue was redissolved in CH2Cl2 (10 ml)
5. 5
   기타evaporated in vacuo
6. 6
   기타partitioned
7. 7
   건조dried over Na2SO4
8. 8
   여과filtered
9. 9
   기타the filtrate evaporated in vacuo to a brown gum
10. 10
    기타The gum was purified by flash silica-gel chromatography
11. 11
    세척eluted with 3%MeOH/CHCl3

실험 절차

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.

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