Hydrochloric Acid → 1-Methyl-5-(3-propionylpropyl)thio-1,2,3,4-tetrazole

HRID 1758321Notes

Reaction equation

HRID 1758321 reaction equation
[Mg].II.[CH3:4][N:5]1[C:9]([S:10][CH2:11][CH2:12][CH2:13]Cl)=[N:8][N:7]=[N:6]1.C(Br)C.C(#N)CC.Cl.[O:23]1C[CH2:26][CH2:25][CH2:24]1>O>[CH3:4][N:5]1[C:9]([S:10][CH2:11][CH2:12][CH2:13][C:24](=[O:23])[CH2:25][CH3:26])=[N:8][N:7]=[N:6]1

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 807IodineHCID 6332Ethyl BromideHCID 7854PropionitrileHCID 8028Tetrahydrofuran3×HCID 5462224MagnesiumHCID 128033761-Methyl-5-(3-chloropropyl)thio-1,2,3,4-tetrazole2×

Product 1

HCID 130916231-Methyl-5-(3-propionylpropyl)thio-1,2,3,4-tetrazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Magnesium (0.3 g) is suspended in dried tetrahydrofuran (5 ml). To the suspension is added a small piece of iodine with stirring in nitrogen gas flow, and further added 1-methyl-5-(3-chloropropyl)thio-1,2,3,4-tetrazole (0.3 g). To the mixture is added ethyl bromide (0.1 ml), and the reaction is started by heating the mixture from outside. A solution of 1-methyl-5-(3-chloropropyl)thio-1,2,3,4-tetrazole (1.8 g) in dried tetrahydrofuran (15 ml) is additionally added dropwise to the mixture. After the solution is added, the mixture is refluxed for 1 hour. To the obtained Grignard reagent is added dropwise a solution of propionitrile (0.5 g) in dried tetrahydrofuran (5 ml) with stirring under ice-cooling, and the mixture is stirred for 3 hours at room temperature. To the mixture is added 1 N-HCl (20 ml) under ice-cooling and the mixture is stirred for 1 hour. The reaction mixture is diluted with water and extracted with chloroform. The chloroform solution is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride and dried over sodium sulfate. After chloroform is distilled off, the residue is purified by silica gel column chromatography (Kieselgel 60) and eluted with benzene-ether (10:1) to give 1-methyl-5-(3-propionylpropyl)thio-1,2,3,4-tetrazole (0.5 g) as colorless liquid, nD25 =1.5042.

Workup

  1. temperatureby heating the mixture from outside
  2. additionAfter the solution is added
  3. temperaturethe mixture is refluxed for 1 hour
  4. temperaturecooling
  5. stirringthe mixture is stirred for 3 hours at room temperature
  6. temperaturecooling
  7. stirringthe mixture is stirred for 1 hour
  8. extractionextracted with chloroform
  9. washThe chloroform solution is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  10. dry with materialdried over sodium sulfate
  11. distillationAfter chloroform is distilled off
  12. customthe residue is purified by silica gel column chromatography (Kieselgel 60)
  13. washeluted with benzene-ether (10:1)

Sources & evidence

ORD record
ord-6e01c3aa35804e39b5a1fed40ca136d5
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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