反応 #63528

反応方程式

2-(3,4-dimethoxyphenyl)ethylamine

DBU

4-(1-Methyl-1,2,3,4-tetrazol-5-yl)thio-butyric acid

isobutyl chloroformate

→

N-[2-(3,4-dimethoxyphenyl)ethyl]-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide

収率 41.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   温度cooling
2. 2
   workup.STIRRINGthe mixture is further stirred at room temperature for 2 hours
3. 3
   workup.DISTILLATIONAfter the solvent is distilled off under reduced pressure
4. 4
   抽出the resulting residue is extracted with chloroform
5. 5
   洗浄The chloroform layer is washed with 5% aqueous hydrochloric acid
6. 6
   乾燥an aqueous saturated sodium hydrogen carbonate solution and an aqueous saturated sodium chloride solution and dried over anhydrous sodium sulfate
7. 7
   workup.DISTILLATIONAfter distilling off chloroform
8. 8
   洗浄the residue is subjected to column chromatography (Wakogel C-200, eluting agent, chloroform)

実験手順

4-(1-Methyl-1,2,3,4-tetrazol-5-yl)thio-butyric acid (45 mmole) is dissolved in tetrahydrofuran (50 ml), and thereto is added DBU (50 mmole). To the mixture is added dropwise with stirring isobutyl chloroformate (50 mmole) under ice-cooling and the mixture is stirred at room temperature for 30 minutes. To the mixture is added dropwise 2-(3,4-dimethoxyphenyl)ethylamine (54 mmole) and the mixture is further stirred at room temperature for 2 hours. After the solvent is distilled off under reduced pressure, the resulting residue is extracted with chloroform. The chloroform layer is washed with 5% aqueous hydrochloric acid, an aqueous saturated sodium hydrogen carbonate solution and an aqueous saturated sodium chloride solution and dried over anhydrous sodium sulfate. After distilling off chloroform, the residue is subjected to column chromatography (Wakogel C-200, eluting agent, chloroform) to isolate N-[2-(3,4-dimethoxyphenyl)ethyl]-4-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (yield: 41%) which is recrystallized from hexane-chloroform, colorless flaks, m.p. 70.5°-71.5° C.

出典