Water → HCID 178527651, compound

HRID 1390885Notes

Reaction equation

HRID 1390885 reaction equation
[K].[S:2]([CH2:6][CH2:7][NH:8][C:9](=[S:12])SC)([OH:5])(=[O:4])=[O:3].[N-:13]=[N+:14]=[N-:15].[Na+].O>CC(C)=O>[S:2]([CH2:6][CH2:7][N:8]1[C:9]([SH:12])=[N:15][N:14]=[N:13]1)([OH:5])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86735067HCID 86735067, compound

Product 1

HCID 178527651HCID 178527651, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 21.5 g. (0.087 mol.) of methyl 2-sulfoethyldithiocarbamate potassium salt (0.5 hydrate) and 7.16 g. (0.11 mol.) of sodium azide in 200 ml. of water was refluxed for two hours. The solution was cooled to 25° and extracted with ethyl acetate. The aqueous phase was treated with Amberlite IR-120H resin, washed with ether and evaporated to give an oil. The oil was dissolved in acetone, the solution was filtered and the filtrate was evaporated to dryness to give 1-(2-sulfoethyl)-tetrazole-5-thiol. The thiol was dissolved in isopropanol, cyclohexylamine was added until pH 8-9 and acetonitrile was added to give 1-(2-sulfoethyl)tetrazole-5-thiol as the di-cyclohexylamine salt.

Workup

  1. additionA mixture of 21.5 g
  2. temperatureThe solution was cooled to 25°
  3. extractionextracted with ethyl acetate
  4. additionThe aqueous phase was treated with Amberlite IR-120H resin
  5. washwashed with ether
  6. customevaporated
  7. customto give an oil
  8. filtrationthe solution was filtered
  9. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-a89744559dcb49cc8f3e6f566def0f59
Source dataset
uspto-grants-1979_02
Patent number
US04140694

Reaction notes

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