Sodium Hydroxide → 1-Methyl-5-(3-cyclohexylcarbonylpropyl)thio-1,2,3,4-tetrazole

HRID 1758309Notes

Reaction equation

HRID 1758309 reaction equation
[CH3:1][N:2]1[C:6](Cl)=[N:5][N:4]=[N:3]1.N[C:9](N)=[S:10].[CH:12]1([C:18]([CH2:20][CH2:21]CBr)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[OH-].[Na+]>C(O)C>[CH3:1][N:2]1[C:6]([S:10][CH2:9][CH2:21][CH2:20][C:18]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:19])=[N:5][N:4]=[N:3]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 205098273-Bromopropyl cyclohexyl ketoneHCID 205098305-chloro-1-methyl-1H-1,2,3,4-tetrazole

Product 1

HCID 130916241-Methyl-5-(3-cyclohexylcarbonylpropyl)thio-1,2,3,4-tetrazoleYield 26.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Methyl-5-chloro-1,2,3,4-tetrazole (2.4 g) is dissolved in ethanol (30 ml). Thiourea (1.5 g) is added to the solution and the mixture is refluxed for 2 hours. 3-Bromopropyl cyclohexyl ketone (4.7 g) and 10% aqueous sodium hydroxide (10 ml) are added to the mixture is further refluxed for 3 hours. Ethanol is distilled off and water is added to the residue. The mixture is extracted with chloroform. The chloroform solution is washed with water and then saturated aqueous sodium chloride and dried over magnesium sulfate. Chloroform is distilled off and the residue is purified by column chromatography (Wakogel C-200, eluant: chloroform) to obtain 1-methyl-5-(3-cyclohexylcarbonylpropyl)thio-1,2,3,4-tetrazole (1.4 g) as colorlss liquid, nD12 =1.5267.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. temperatureis further refluxed for 3 hours
  3. distillationEthanol is distilled off
  4. additionwater is added to the residue
  5. extractionThe mixture is extracted with chloroform
  6. washThe chloroform solution is washed with water
  7. dry with materialsaturated aqueous sodium chloride and dried over magnesium sulfate
  8. distillationChloroform is distilled off
  9. customthe residue is purified by column chromatography (Wakogel C-200, eluant: chloroform)

Sources & evidence

ORD record
ord-9bb3e9f7244e4aeabfce5d92d9025026
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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