反応 #78506

反応方程式

N-(4-cyanophenyl)glycine

3-amino-4-methylaminobenzoic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

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crude product

1-Methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   温度the mixture was refluxed for a further five hours
2. 2
   workup.DISTILLATIONThen the solvent was distilled off in vacuo
3. 3
   workup.DISSOLUTIONthe residue was dissolved in 150 mL of glacial acetic acid
4. 4
   温度refluxed for one hour
5. 5
   workup.DISTILLATIONThen the glacial acetic acid was distilled off in vacuo
6. 6
   workup.DISSOLUTIONthe residue was dissolved in about 300 mL of dichloromethane
7. 7
   洗浄the solution was washed twice with about 150 mL water
8. 8
   乾燥dried over sodium sulfate
9. 9
   その他After evaporation of the solvent

実験手順

6.17 g (0.035 mol) of N-(4-cyanophenyl)glycine and 5.68 g (0.035 mol) of N,N′-carbonyldiimidazole were refluxed in 300 mL of tetrahydrofuran for 30 minutes, then 10.6 g (0.032 mol) of 3-amino-4-methylaminobenzoic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide were added, and the mixture was refluxed for a further five hours. Then the solvent was distilled off in vacuo, the residue was dissolved in 150 mL of glacial acetic acid and refluxed for one hour. Then the glacial acetic acid was distilled off in vacuo, the residue was dissolved in about 300 mL of dichloromethane, the solution was washed twice with about 150 mL water and then dried over sodium sulfate. After evaporation of the solvent, the crude product thus obtained was purified by column chromatography (800 g silica gel; eluant: dichloromethane with 1-2% ethanol). Yield: 8.5 g (57% of theory); Rf value: 0.51 (silica gel; dichloromethane/ethanol=19:1).

出典