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

HRID 1719581Notes

Reaction equation

HRID 1719581 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(1-Cyclohexyl-1,2,3,4-tetrazol-5-yl)thio-butyric 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)thio-butyramide (yield: 47%), colorless liquid, nD18 =1.5290.

Workup

  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)

Sources & evidence

ORD record
ord-9a662a61ab2140e1901b943ffe2e9557
Source dataset
uspto-grants-1985_09
Patent number
US04540703

Reaction notes

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