Sodium Azide → HCID 178474793, compound

HRID 2286991Notes

Reaction equation

HRID 2286991 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[S:12])SC)(=[O:3])[CH3:2].[N-:13]=[N+:14]=[N-:15].[Na+]>O1CCOCC1.O>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][N:8]1[C:9]([SH:12])=[N:15][N:14]=[N:13]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 23324174Methyl (3-acetamidopropyl)carbamodithioate

Product 1

HCID 178474793HCID 178474793, compoundYield 48.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of a solution of methyl N-(3-acetamidopropyl)dithiocarbamate (193 g) in dioxane (610 ml) and a solution of sodium azide (79.42 g) in water (500 ml) was refluxed under stirring for 4 hours. Dioxane was distilled off and the remaining aqueous layer was washed with diethyl ether (150 ml×2), adjusted to pH 1 with 17.5% hydrochloric acid, and cooled in an ice bath. Precipitates were collected by filtration and washed with ice-water to give white powder of 1-(3-acetamidopropyl)-1H-tetrazol-5-thiol (91.75 g), mp. 152° to 154° C.

Workup

  1. distillationDioxane was distilled off
  2. washthe remaining aqueous layer was washed with diethyl ether (150 ml×2)
  3. temperaturecooled in an ice bath
  4. customPrecipitates
  5. filtrationwere collected by filtration
  6. washwashed with ice-water

Sources & evidence

ORD record
ord-931c538b541841779117b6bdcdd834b1
Source dataset
uspto-grants-1981_05
Patent number
US04268509

Reaction notes

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