N-Ethyl cyclohexylamine → HCID 54210954, 화합물

HRID 35251

반응식

HRID 35251 반응식
[C: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)[CH:6]=[CH:5][CH:4]=[CH:3][CH: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]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=[N:9][N:10]=1)[CH3:24]

참가 물질

6

반응물 4

HCID 21609N-Ethyl cyclohexylamineHCID 62365Isobutyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178526181HCID 178526181, 화합물

생성물 1

HCID 54210954HCID 54210954, 화합물수율 43%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-(1-Phenyl-1,2,3,4-tetrazol-5-yl)thio-butyric acid (45 mmol) 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. The mixture is stirred at room temperature for 30 minutes. To the mixture is added dropwise N-ethylcyclohexylamine (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 solution 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 chromatogrophy (Wakogel C-200, eluting solvent, chloroform) to isolate N-ethyl-N-cyclohexyl-4-(1-phenyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (yield: 43%), colorless liquid, nD18 =1.5590.

후처리

  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 solution 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 chromatogrophy (Wakogel C-200, eluting solvent, chloroform)

출처 및 근거

ORD 기록
ord-afe70d54050b460998d3b044f17e9b47
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04766120

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