Water → HCID 178444732, compound

HRID 2412785Notes

Reaction equation

HRID 2412785 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].O.[CH2:6]([NH:12][C:13](=[S:16])SC)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>C(O)C>[CH2:6]([N:12]1[C:13]([SH:16])=[N:3][N:2]=[N:1]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 15917037Methyl hexyldithiocarbamate

Product 1

HCID 178444732HCID 178444732, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Sodium azide (155.9 g.) and water (0.8 l.) were added under stirring to a solution of methyl N-hexyldithiocarbamate (430 g.) in ethanol (1.7 l.) and the resulting mixture was refluxed for 3.5 hours at 90° C. Ethanol was distilled off from the reaction mixture and the residue was washed with diethyl ether (1 l.), adjusted to pH 2.0 with conc. hydrochloric acid and extracted with diethyl ether (1 l.). The extract was washed with water, dried over magnesium sulfate and concentrated to give an oil of 1-hexyl-1H-tetrazole-5-thiol (431.3 g.).

Workup

  1. distillationEthanol was distilled off from the reaction mixture
  2. washthe residue was washed with diethyl ether (1 l.)
  3. extractionextracted with diethyl ether (1 l.)
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-27ca43c30aed4462a2db0e46c8cf720d
Source dataset
uspto-grants-1985_01
Patent number
US04493833

Reaction notes

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