Thionyl Chloride → HCID 22938485, compound

HRID 856720Notes

Reaction equation

HRID 856720 reaction equation
O[CH2:2][C:3]1[N:4]=[N:5][N:6]([CH2:8][CH2:9][CH3:10])[CH:7]=1.S(Cl)([Cl:13])=O>>[Cl:13][CH2:2][C:3]1[N:4]=[N:5][N:6]([CH2:8][CH2:9][CH3:10])[CH:7]=1

Participants

3

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. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b8e15d6d67554dbfaeee1ffc5bf35921
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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