Sodium Thiosulfate → HCID 22938752, compound

HRID 856719Notes

Reaction equation

HRID 856719 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[CH2:7]([N:10]1[CH:14]=[C:13]([C:15](OC)=[O:16])[N:12]=[N:11]1)[CH2:8][CH3:9].S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[OH:16][CH2:15][C:13]1[N:12]=[N:11][N:10]([CH2:7][CH2:8][CH3:9])[CH:14]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 21226445Aluminium lithium hydrideHCID 22938529HCID 22938529, compound

Product 1

HCID 22938752HCID 22938752, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of aluminum lithium hydride (0.58 g) in THF (51.4 ml) was added dropwise a solution of methyl 1-propyl-1,2,3-triazole-4-carboxylate (2.6 g) in THF (26 ml) at 0° C. The mixture was stirred for 1 hour at room temperature, and an aqueous solution of saturated sodium thiosulfate was added to the mixture at 0° C. The mixture was filtered with Celite, and washed with ethanol. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 4-hydroxymethyl-1-propyl-1,2,3-triazole (1.9 g). To 4-hydroxymethyl-1-propyl-1,2,3-triazole (1.9 g) was added thionyl chloride (32 ml) at 0° C., and the mixture was heated to reflux for 1 hour. After allowing the mixture to be cooled to room temperature, the solvent was removed under reduced pressure, to give 4-chloromethyl-1-propyl-1,2,3-triazole (1.75 g).

Workup

  1. filtrationThe mixture was filtered with Celite
  2. washwashed with ethanol
  3. customThe solvent was removed under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6d6f93c1d8db4bc994ec1f6a135dfcc0
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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