Sodium Azide → HCID 178474792, compound

HRID 543842Notes

Reaction equation

HRID 543842 reaction equation
C(NC(C)CNC(=S)SC)(=O)C.[C:13]([NH:16][CH2:17][CH:18]([NH:20][C:21](=[S:24])SC)[CH3:19])(=[O:15])[CH3:14].[N-:25]=[N+:26]=[N-:27].[Na+]>O1CCOCC1.O>[C:13]([NH:16][CH2:17][CH:18]([N:20]1[C:21]([SH:24])=[N:27][N:26]=[N:25]1)[CH3:19])(=[O:15])[CH3:14]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 23324130HCID 23324130, compoundHCID 23324216HCID 23324216, compound

Product 1

HCID 178474792HCID 178474792, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl N-(2-acetamidopropyl)dithiocarbamate and methyl N-[1-(acetamidomethyl)ethyl]dithiocarbamate (100 g) in dioxane (300 ml) and a solution of sodium azide (41 g) in water (270 ml) were stirred for 4.5 hours under reflux. The reaction mixture was concentrated to half volume under reduced pressure, washed with diethyl ether and acidified with concentrated hydrochloric acid. The resulting precipitate was collected by filtration and washed with diethyl ether to give pale yellow powder of 1-[1-(acetamidomethyl)ethyl]-1H-tetrazole-5-thiol (26.32 g), mp 176° to 178° C.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated to half volume under reduced pressure
  3. washwashed with diethyl ether
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-4a08fa8c01734debb7d77109fe870603
Source dataset
uspto-grants-1984_05
Patent number
US04447429

Reaction notes

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