반응 #2377772

반응 방정식

water

ethyl chlorocarbonate

2-Methyl-5-methylsulfonyl-2,3-dihydrobenzofuran-7-carboxylic acid

1-ethyl-2-aminomethylpyrrolidine

→

N-(1-ethyl-2-pyrrolidinylmethyl)-2-methyl-5-methylsulfonyl-2,3-dihydrobenzofuran-7-carboxamide hydrochloride

용매

dimethylformamide

acetone

triethylamine

반응 조건

후처리

1. 1
   workup.ADDITIONis added
2. 2
   workup.STIRRINGthe solution is stirred for one hour
3. 3
   workup.STIRRINGthe reactant is stirred for one and a half hours
4. 4
   workup.DISTILLATIONAfter excess triethylamine and acetone are distilled off under reduced pressure
5. 5
   기타the residue obtained
6. 6
   추출extracted three times with ethyl acetate
7. 7
   세척The extract layer is washed with aqueous sodium bicarbonate solution and water
8. 8
   기타dried
9. 9
   workup.DISTILLATIONThe ethyl acetate is distilled off under diminished pressure
10. 10
    workup.DISSOLUTIONthe resulting residue is again dissolved in chloroform
11. 11
    workup.DISTILLATIONExcess hydrochloric acid gas and chloroform are distilled off under reduced pressure
12. 12
    workup.DISSOLUTIONthe resulting residue is dissolved into 35-40 ml of isopropanol
13. 13
    여과filtered
14. 14
    workup.ADDITIONTo the filtrate solution is added 110-120 ml of ethyl acetate
15. 15
    온도the system is cooled with ice

실험 절차

2-Methyl-5-methylsulfonyl-2,3-dihydrobenzofuran-7-carboxylic acid, 5.0 g, is dissolved in a mixed solvent of 40 ml of dimethylformamide and 20 ml of acetone, 6.5 ml of triethylamine is added, and the whole is stirred. At room temperature, 2.3 g of ethyl chlorocarbonate is added and the solution is stirred for one hour. Thereafter, 3.0 g of 1-ethyl-2-aminomethylpyrrolidine is added, and the reactant is stirred for one and a half hours and allowed to stand for 15 hours. After excess triethylamine and acetone are distilled off under reduced pressure, the residue obtained is poured into 300-400 ml of water and extracted three times with ethyl acetate. The extract layer is washed with aqueous sodium bicarbonate solution and water and dried. The ethyl acetate is distilled off under diminished pressure and the resulting residue is again dissolved in chloroform and hydrochloric acid is blown into the solution. Excess hydrochloric acid gas and chloroform are distilled off under reduced pressure and the resulting residue is dissolved into 35-40 ml of isopropanol and filtered. To the filtrate solution is added 110-120 ml of ethyl acetate and the system is cooled with ice to give crystals of N-(1-ethyl-2-pyrrolidinylmethyl)-2-methyl-5-methylsulfonyl-2,3-dihydrobenzofuran-7-carboxamide hydrochloride, m.p. 186°-189° C.

출처