Sodium Azide → HCID 178521216, compound

HRID 1284624Notes

Reaction equation

HRID 1284624 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][NH:13][C:14](=[S:17])SC)[CH2:6][CH2:5]1.[N-:18]=[N+:19]=[N-:20].[Na+]>O.C(O)C>[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][N:13]2[C:14]([SH:17])=[N:20][N:19]=[N:18]2)[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 20252215HCID 20252215, compound

Product 1

HCID 178521216HCID 178521216, compoundYield 28.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl N-[3-[4-(2-hydroxy-ethyl)-1-piperazinyl]-propyl]-dithiocarbamate (4.8 g) in a mixture of water (15 ml) and ethanol (10 ml) as added sodium azide (1.5 g). The resulting mixture was refluxed with stirring for 4 hours. The reaction mixture was concentrated under reduced pressure. The concentrate was disolved in water and the solution was washed successively with ethyl acetate and diethyl ether and then evaporated. To the residue was added ethanol and the mixture was filtered. The filtrate was evaporated under reduced pressure. The residue was recrystallized from isopropyl alcohol to give 1-[3-[4-(2-hydroxy-ethyl)-1-piperazinyl]propyl]-1H-tetrazole-5-thiol (1.35 g).

Workup

  1. temperatureThe resulting mixture was refluxed
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washthe solution was washed successively with ethyl acetate and diethyl ether
  4. customevaporated
  5. additionTo the residue was added ethanol
  6. filtrationthe mixture was filtered
  7. customThe filtrate was evaporated under reduced pressure
  8. customThe residue was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-1522d374f1384d2e8ae83dd43d589c9c
Source dataset
uspto-grants-1986_01
Patent number
US04563524

Reaction notes

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