N-Ethyl cyclohexylamine → HCID 54167384, 화합물

HRID 35252

반응식

HRID 35252 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 54167384HCID 54167384, 화합물수율 52%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b367f873217548f6832be636986c31b9
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04766120

연결된 노트

불러오는 중…