반응 #78488

반응 방정식

2-[N-(4-cyanophenyl)aminomethyl]benzothiazole-5-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

hydrogen chloride

dichloromethane ethanol

ammonium carbonate

→

2-[N-(4-amidinophenyl)aminomethyl]benzothiazole-5-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

용매

ethanol

반응 조건

후처리

1. 1
   기타at room temperature
2. 2
   workup.DISTILLATIONThen the solvent was distilled off at a maximum bath temperature of 30° C.
3. 3
   workup.DISTILLATIONthe solvent was distilled off in vacuo
4. 4
   기타the crude product was purified by flash chromatography (silica gel; gradient: water/methanol=19:1 to 4:1)
5. 5
   기타When the eluates are evaporated down the desired compound
6. 6
   기타is obtained as a white foam

실험 절차

1.1 g (2.27 mmol) of 2-[N-(4-cyanophenyl)aminomethyl]benzothiazole-5-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide was stirred in 100 mL of ethanol saturated with hydrogen chloride for 5 hours, first at 0° C. and then at room temperature, until no more starting material could be detected by thin layer chromatography. Then the solvent was distilled off at a maximum bath temperature of 30° C. and the oily residue was taken up in 100 mL of absolute ethanol and mixed with 1.6 g (22 mmol) of ammonium carbonate. After 18 hours stirring at room temperature, the solvent was distilled off in vacuo and the crude product was purified by flash chromatography (silica gel; gradient: water/methanol=19:1 to 4:1). When the eluates are evaporated down the desired compound is obtained as a white foam. Yield: 0.77 g (63% of theory), C27H27N5O3S (501.60); Rf value: 0.19 (silica gel; dichloromethane/ethanol=3:7); mass spectrum: (M+H)+=502.

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