Thionyl Chloride → HCID 22938552, compound

HRID 856795Notes

Reaction equation

HRID 856795 reaction equation
O[CH2:2][C:3]1[N:7]([CH2:8][C:9]#[CH:10])[CH:6]=[N:5][CH:4]=1.S(Cl)([Cl:13])=O>>[ClH:13].[Cl:13][CH2:2][C:3]1[N:7]([CH2:8][C:9]#[CH:10])[CH:6]=[N:5][CH:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 22938533HCID 22938533, compound

Product 1

HCID 22938552HCID 22938552, compound

Conditions

Temperature
90 °C

Procedure

To 5-hydroxymethyl-1-(2-propyn-1-yl)imidazole (8.0 g) was added by portions thionyl chloride (40 ml) at 0° C., and the mixture was heated for 30 minutes under nitrogen atmosphere at 90° C. The mixture was allowed to be at room temperature. The solvent was distilled off under reduced pressure, and the obtained residue was dissolved in methanol, and then, the solvent was distilled off again under reduced pressure. The obtained solid was recrystalized from ethyl acetate, to give 5-chloromethyl-1-(2-propyn-1-yl)imidazole hydrochloride (9.8 g) as colorless crystals.

Workup

  1. customto be at room temperature
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe obtained residue was dissolved in methanol
  4. distillationthe solvent was distilled off again under reduced pressure
  5. customThe obtained solid was recrystalized from ethyl acetate

Sources & evidence

ORD record
ord-d0f89978bc6e4786b297ffcdfcac1962
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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