Cyclohexyl bromide → HCID 13061936, compound

HRID 1758327Notes

Reaction equation

HRID 1758327 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][SH:11])=[N:5][N:4]=[N:3]1.[CH:12]1(Br)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>[OH-].[Na+].CC(C)=O>[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][S:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:5][N:4]=[N:3]1

Participants

5

Reactant 2

HCID 7960Cyclohexyl bromideHCID 20509856HCID 20509856, compound

Product 1

HCID 13061936HCID 13061936, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 14798Sodium HydroxideSolvent

Procedure

1-Methyl-5-(3-mercaptopropyl)thio-1,2,3,4-tetrazole (1.9 g) is dissolved in 1 N aqueous sodium hydroxide (30 ml), and thereto is added dropwise a solution of cyclohexyl bromide (2.0 g) in acetone (20 ml) with stirring under ice-cooling. After the addition, the mixture is stirred at room temperature for 3 hours. Acetone is distilled off and water is added to the residue, and the mixture is extracted with ether. The ether solution is washed with diluted aqueous sodium hydroxide and saturated aqueous sodium chloride, and dried over sodium sulfate. After ether is distilled off, the residue is purified by column chromatography (Kieselgel 60), followed by eluting with n-hexane-ether (4:1) to give 1-methyl-5-(3-cyclohexylthiopropyl)thio-1,2,3,4-tetrazole (1.5 g), colorless liquid, nD18 =1.5433.

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. stirringthe mixture is stirred at room temperature for 3 hours
  4. distillationAcetone is distilled off
  5. additionwater is added to the residue
  6. extractionthe mixture is extracted with ether
  7. washThe ether solution is washed with diluted aqueous sodium hydroxide and saturated aqueous sodium chloride
  8. dry with materialdried over sodium sulfate
  9. distillationAfter ether is distilled off
  10. customthe residue is purified by column chromatography (Kieselgel 60)
  11. washby eluting with n-hexane-ether (4:1)

Sources & evidence

ORD record
ord-535fb39431f34229b0af718833c9e057
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

Loading…