Sodium Azide → HCID 178527917, compound

HRID 1284632Notes

Reaction equation

HRID 1284632 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][NH:16][C:17](=[S:20])SC)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:21]=[N+:22]=[N-:23].[Na+]>O.C(O)C>[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][N:16]3[C:17](=[S:20])[NH:23][N:22]=[N:21]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 12802957methyl N-[3-(4-phenyl-1-piperazinyl)propyl]dithiocarbamate

Product 1

HCID 178527917HCID 178527917, compoundYield 25.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl N-[3-(4-phenyl-1-piperazinyl)propyl]dithiocarbamate (12.9 g) in a mixture of water (20 m) and ethanol (30 m) was added sodium azide (3.6 g). The resulting mixture was refluxed with stirring for 4.5 hours. The reaction mixture was concentrated under reduced pressure. After the addition of water to the residue, the mixture was washed successively with ethyl acetate and diethyl ether and then evaporated. To the residue was added ethanol (100 m) and the mixture was filtered. The filtrate was evaporated under reduced pressure. The residue was recrystallized from isopropyl alcohol twice to give 1-[3-(4-phenyl-1-piperazinyl)propyl]-4,5-dihydro-1H-tetrazole-5-thione (3.2 g), mp. 200° to 205° C.

Workup

  1. temperatureThe resulting mixture was refluxed
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionAfter the addition of water to the residue
  4. washthe mixture was washed successively with ethyl acetate and diethyl ether
  5. customevaporated
  6. additionTo the residue was added ethanol (100 m)
  7. filtrationthe mixture was filtered
  8. customThe filtrate was evaporated under reduced pressure
  9. customThe residue was recrystallized from isopropyl alcohol twice

Sources & evidence

ORD record
ord-297e08bfaca0495aa21d1c597fdba686
Source dataset
uspto-grants-1986_01
Patent number
US04563524

Reaction notes

Loading…