Potassium Carbonate → Cyclohexanecarboxamide, N-ethyl-N-(3-((1-methyl-1H-tetrazol-5-yl)thio)propyl)-

HRID 1758339Notes

Reaction equation

HRID 1758339 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:12][CH3:13])=[N:5][N:4]=[N:3]1.C(=O)([O-])[O-].[K+].[K+].[CH:20]1([C:26](Cl)=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>CC(C)=O.O>[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[C:26]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:27])=[N:5][N:4]=[N:3]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 75938Cyclohexanecarbonyl chlorideHCID 20509877HCID 20509877, compound

Product 1

HCID 3061969Cyclohexanecarboxamide, N-ethyl-N-(3-((1-methyl-1H-tetrazol-5-yl)thio)propyl)-Yield 58.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

1-Methyl-5-[3-(N-ethylamino)propylthio]-1,2,3,4-tetrazole (1 g) is dissolved in a mixture of acetone (50 ml) and water (10 ml). To the mixture is added potassium carbonate (0.7 g) and thereto is added dropwise with stirring cyclohexanecarboxylic acid chloride (0.9 g) under ice-cooling. Stirring is continued for 2 hours under ice-cooling. After acetone is distilled off, water is added to the resulting residue and the mixture is extracted with chloroform. The chloroform solution is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride and dried over sodium sulfate. Chloroform is distilled off and then the residue is purified by column chromatography (Wakogel C-200), followed by eluting with chloroform to give 1-methyl-5-[3-(N-ethyl-N-cyclohexylcarbonylamino)propylthio]-1,2,3,4-tetrazole (0.9 g), colorless liquid, nD23.5 =1.5267.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. distillationAfter acetone is distilled off
  4. additionwater is added to the resulting residue
  5. extractionthe mixture is extracted with chloroform
  6. washThe chloroform solution is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  7. dry with materialdried over sodium sulfate
  8. distillationChloroform is distilled off
  9. customthe residue is purified by column chromatography (Wakogel C-200)
  10. washby eluting with chloroform

Sources & evidence

ORD record
ord-fc0fa7cd4d4645789a4d37cd978e16bf
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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