Sodium Thiosulfate → HCID 22938707, compound

HRID 856716Notes

Reaction equation

HRID 856716 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[CH2:7]([N:10]1[N:14]=[C:13]([C:15](OC)=[O:16])[CH:12]=[N:11]1)[CH2:8][CH3:9].S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[OH:16][CH2:15][C:13]1[CH:12]=[N:11][N:10]([CH2:7][CH2:8][CH3:9])[N:14]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 21226445Aluminium lithium hydrideHCID 22938523HCID 22938523, compound

Product 1

HCID 22938707HCID 22938707, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of aluminum lithium hydride (1.57 g) in THF (140 ml) was added dropwise methyl 2-propyl-1,2,3-triazole-4-carboxylate (7.0 g) in. THF (70 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-2-propyl-1,2,3-triazole (5.9 g). To 4-hydroxymethyl-2-propyl-1,2,3-triazole (4.0 g), thionyl chloride (32 ml) was added to the mixture 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-2-propyl-1,2,3-triazole (4.2 g).

Workup

  1. customat 0° C
  2. filtrationThe mixture was filtered with Celite
  3. washwashed with ethanol
  4. customThe solvent was removed under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c8de837da4ec495ab2ac298eceb9758d
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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