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

HRID 1758318Notes

Reaction equation

HRID 1758318 reaction equation
[Mg:1].[CH2:2]([Br:4])[CH3:3].[CH3:5][N:6]1[C:10]([S:11]CC[CH2:14][C:15]#N)=[N:9][N:8]=[N:7]1.Cl.[O:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>O>[CH2:14]([Mg:1][Br:4])[CH3:15].[CH3:5][N:6]1[C:10]([S:11][CH2:22][CH2:21][CH2:20][C:19](=[O:18])[CH2:2][CH3:3])=[N:9][N:8]=[N:7]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 8028Tetrahydrofuran2×HCID 5462224MagnesiumHCID 20509842HCID 20509842, compound

Product 2

HCID 130916231-Methyl-5-(3-propionylpropyl)thio-1,2,3,4-tetrazoleHCID 178418443HCID 178418443, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethylmagnesium bromide is prepared from magnesium (0.25 g), ethyl bromide (1.2 g) and dried tetrahydrofuran (10 ml). To the product is added dropwise a solution of 4-(1-methyl-1,2,3,4-tetrazol-5-yl)thiobutyronitrile (1.8 g) in dried tetrahydrofuran (10 ml) with stirring under ice-cooling. After the solution is added, the mixture is stirred at room temperature for 3 hours. To the mixture is added 1 N-HCl (50 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 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. temperaturecooling
  2. additionAfter the solution is added
  3. stirringthe mixture is stirred at room temperature for 3 hours
  4. temperaturecooling
  5. stirringthe mixture is stirred for 1 hour
  6. extractionextracted with chloroform
  7. washThe chloroform solution is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  8. dry with materialdried over sodium sulfate
  9. distillationAfter chloroform is distilled off
  10. customthe residue is purified by column chromatography (Kieselgel 60)
  11. washeluted with benzene-ether (10:1)

Sources & evidence

ORD record
ord-bd2cd9950e5c41f2ab8ed5debde0a544
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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