Water → HCID 178444732, compound

HRID 1659781Notes

Reaction equation

HRID 1659781 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-43e9c1b6de8b4c749f294cdcaf08dd79
Source dataset
uspto-grants-1981_12
Patent number
US04304770

Reaction notes

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