Sodium Azide → HCID 178474869, compound

HRID 1395785Notes

Reaction equation

HRID 1395785 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH:7][C:8](=[S:11])SC)(=[O:3])[CH3:2].[N-:12]=[N+:13]=[N-:14].[Na+]>O1CCOCC1.O>[C:1]([NH:4][CH2:5][CH2:6][N:7]1[C:8]([SH:11])=[N:14][N:13]=[N:12]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 20501582Methyl 2-acetamidoethyldithiocarbamate

Product 1

HCID 178474869HCID 178474869, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl N-(2-acetamidoethyl)dithiocarbamate (12.6 g.) in dioxane (40 ml.) was added a solution of sodium azide (6.4 g.) in water (40 ml.), and the mixture was heated under reflux for 4 hours. After dioxane was removed from the resultant mixture under reduced pressure, the residue was washed with ether (350 ml.) and adjusted to pH 1 with 10% hydrochloric acid. After the resultant solution was extracted with ethyl acetate (1.5 l.), the extract was dried over magnesium sulfate and the solvent was evaporated to dryness to give 1-(2-acetamidoethyl)-1H-tetrazole-5-thiol (5.3 g.) having m.p. 137.5° to 139.5° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customAfter dioxane was removed from the resultant mixture under reduced pressure
  4. washthe residue was washed with ether (350 ml.)
  5. extractionAfter the resultant solution was extracted with ethyl acetate (1.5 l.)
  6. dry with materialthe extract was dried over magnesium sulfate
  7. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-bd19580bbca44d49b75f083b31bf5605
Source dataset
uspto-grants-1980_05
Patent number
US04205166

Reaction notes

Loading…