N-Ethyl cyclohexylamine → N-ethyl-N-cyclohexyl-4-[1-(4-ethylphenyl)-1,2,3,4-tetrazol-5-yl]thio-butyramide

HRID 35258

反応式

HRID 35258 の反応式
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH2:14][CH2:15][CH2:16][C:17](O)=[S:18])=[N:12][N:11]=[N:10]2)=[CH:5][CH:4]=1)[CH3:2].[CH2:20]1[CH2:30][CH2:29][N:28]2[C:23](=NC[CH2:26][CH2:27]2)[CH2:22][CH2:21]1.ClC(OCC(C)C)=O.C(NC1CCCCC1)C>O1CCCC1>[CH2:27]([N:28]([CH:23]1[CH2:22][CH2:21][CH2:20][CH2:30][CH2:29]1)[C:17](=[S:18])[CH2:16][CH2:15][CH2:14][C:13]1[N:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[N:10]=[N:11][N:12]=1)[CH3:26]

参加物

6

反応物 4

HCID 21609N-Ethyl cyclohexylamineHCID 62365Isobutyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178436515HCID 178436515、化合物

生成物 1

HCID 54060908N-ethyl-N-cyclohexyl-4-[1-(4-ethylphenyl)-1,2,3,4-tetrazol-5-yl]thio-butyramide収率 43%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4-[1-(4-Ethylphenyl)-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 mmol) under ice-cooling, and the mixture is stirred at room temperature for 30 minutes. To the mixture is added dropwise N-ethyl-cyclohexylamine (54 mmole), and the mixture is further stirred at room temperature for 2 hours. The solvent is distilled off under reduced pressure and 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 then dried over anhydrous sodium sulfate. Chloroform is distilled off and the resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V) to isolate N-ethyl-N-cyclohexyl-4-[1-(4-ethylphenyl)-1,2,3,4-tetrazol-5-yl]thio-butyramide (yield: 43%), colorless liquid, nD19 =1.5533.

後処理

  1. temperaturecooling
  2. stirringthe mixture is further stirred at room temperature for 2 hours
  3. distillationThe solvent is distilled off under reduced pressure
  4. extractionthe resulting residue is extracted with chloroform
  5. washThe chloroform layer is washed with 5% aqueous hydrochloric acid
  6. dry with materialan aqueous saturated sodium hydrogen carbonate solution and an aqueous saturated sodium chloride solution and then dried over anhydrous sodium sulfate
  7. distillationChloroform is distilled off
  8. washthe resulting residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V)

出典と根拠

ORDレコード
ord-9703c3c7166e40c59912450ba1fa4beb
出典データセット
uspto-grants-1988_08
特許番号
US04766120

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