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

HRID 1719580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1719580
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 54167384N-ethyl-N-cyclohexyl-2-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-acetamideAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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 chromatograpy (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.

Aufarbeitung

  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 chromatograpy (Wakogel C-200, eluting solvent, benzene:chloroform=4:1, V/V)

Quellen und Nachweise

ORD-Eintrag
ord-0509fae3f30d4803a0ecbd4187f42f46
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04540703

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