N-Ethyl cyclohexylamine → HCID 54167384、化合物

HRID 978024

反応式

HRID 978024 の反応式
[CH3:1][N:2]1[C:6]([CH2:7][C:8](O)=[S:9])=[N:5][N:4]=[N:3]1.[CH2:11]1[CH2:21][CH2:20][N:19]2[C:14](=NC[CH2:17][CH2:18]2)[CH2:13][CH2:12]1.ClC(OCC(C)C)=O.C(NC1CCCCC1)C>O1CCCC1>[CH2:18]([N:19]([CH:14]1[CH2:13][CH2:12][CH2:11][CH2:21][CH2:20]1)[C:8](=[S:9])[CH2:7][C:6]1[N:2]([CH3:1])[N:3]=[N:4][N:5]=1)[CH3:17]

参加物

6

反応物 4

HCID 21609N-Ethyl cyclohexylamineHCID 62365Isobutyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178482014HCID 178482014、化合物

生成物 1

HCID 54167384HCID 54167384、化合物収率 52%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-(1-Methyl-1,2,3,4-tetrazol-5-yl)thio-acetic 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 N-ethyl-cyclohexylamine under ice-cooling, and the mixture is further stirred at room temperature for 2 hours. After distilling off the solvent 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. Chloroform is distilled off and the residue is subjected to column chromatography (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V) to isolate N-ethyl-N-cyclohexyl-2-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-acetamide (yield: 52%) which is recrystallized from ether-petroleum ether, white prisms, m.p. 69°-71° C.

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture is further stirred at room temperature for 2 hours
  4. distillationAfter distilling off the solvent under reduced pressure
  5. extractionthe resulting residue is extracted with chloroform
  6. washThe chloroform layer is washed with 5% aqueous hydrochloric acid
  7. dry with materialan aqueous saturated sodium hydrogen carbonate solution and an aqueous saturated sodium chloride solution and dried over anhydrous sodium sulfate
  8. distillationChloroform is distilled off
  9. washthe 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-3ee23771c50f4db08a424207bf9f275d
出典データセット
uspto-grants-1987_05
特許番号
US04663323

関連ノート

読み込み中…