Sodium Iodide → 1-methyl-5-[3-(N,N-diethylamino)propylthio]-1,2,3,4-tetrazole

HRID 1758341Notes

Reaction equation

HRID 1758341 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10]Cl)=[N:5][N:4]=[N:3]1.[I-].[Na+].[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15]>CN(C)C=O>[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][N:16]([CH2:17][CH3:18])[CH2:14][CH3:15])=[N:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8021DiethylamineHCID 128033761-Methyl-5-(3-chloropropyl)thio-1,2,3,4-tetrazole

Product 1

HCID 128033771-methyl-5-[3-(N,N-diethylamino)propylthio]-1,2,3,4-tetrazoleYield 24.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Methyl-5-(3-chloropropylthio)-1,2,3,4-tetrazole (3.8 g) is dissolved in dimethylformamide (50 ml). To the mixture are added sodium iodide (3 g) and diethylamine (4.4 g) and the mixture is stirred at 60°-70° C. for 3 hours. Dimethylformamide is distilled off under reduced pressure, and the residue is purified by alumina column chromatography (basic alumina, made by Merk & Co.), followed by eluting with n-hexane to give 1-methyl-5-[3-(N,N-diethylamino)propylthio]-1,2,3,4-tetrazole (1.1 g), colorless liquid, nD25 =1.5040.

Workup

  1. distillationDimethylformamide is distilled off under reduced pressure
  2. customthe residue is purified by alumina column chromatography (basic alumina, made by Merk & Co.)
  3. washby eluting with n-hexane

Sources & evidence

ORD record
ord-c3f55ecedd4441ecbd44b838e8634570
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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