N-Ethyl cyclohexylamine → N-ethyl-N-cyclohexyl-4-(1-cyclohexyl-1,2,3,4-tetrazol-5-yl)thiobutyramide

HRID 35253

反応式

HRID 35253 の反応式
[CH:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH2:14][C:15](O)=[S:16])=[N:10][N:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:18]1[CH2:28][CH2:27][N:26]2[C:21](=NC[CH2:24][CH2:25]2)[CH2:20][CH2:19]1.ClC(OCC(C)C)=O.C(NC1CCCCC1)C>O1CCCC1>[CH2:25]([N:26]([CH:21]1[CH2:20][CH2:19][CH2:18][CH2:28][CH2:27]1)[C:15](=[S:16])[CH2:14][CH2:13][CH2:12][C:11]1[N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:8]=[N:9][N:10]=1)[CH3:24]

参加物

6

反応物 4

HCID 21609N-Ethyl cyclohexylamineHCID 62365Isobutyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178526182HCID 178526182、化合物

生成物 1

HCID 21295420N-ethyl-N-cyclohexyl-4-(1-cyclohexyl-1,2,3,4-tetrazol-5-yl)thiobutyramide収率 47%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4-(1-Cyclohexyl-1,2,3,4-tetrazol-5-yl)thiobutyric 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 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. After distilling off the solvent under reduced pressure, the residue is extracted with chloroform. The chloroform layer is washed with 5% aqueous hydrochloric acid, an aqueous saturated sodium hydrogen carbonate and an aqueous saturated sodium chloride solution and 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-cyclohexyl-1,2,3,4-tetrazol-5-yl)thiobutyramide (yield: 47%), colorless liquid, nD18 =1.5290.

後処理

  1. temperaturecooling
  2. stirringthe mixture is further stirred at room temperature for 2 hours
  3. distillationAfter distilling off the solvent under reduced pressure
  4. extractionthe 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 and an aqueous saturated sodium chloride solution and 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-81306804adb74072a3ef6b37d32c7d65
出典データセット
uspto-grants-1988_08
特許番号
US04766120

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