Sodium Azide → HCID 178474792, compound

HRID 2286996Notes

Reaction equation

HRID 2286996 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-e84079663fd84337b640d1c3358a6e51
Source dataset
uspto-grants-1981_05
Patent number
US04268509

Reaction notes

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