1,3-Dichloroacetone → 1,3-dimethyl-2-[(3-chloro-2-oxopropyl)thio]-1H-imidazolium chloride

HRID 1493286Notes

Reaction equation

HRID 1493286 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][N:4]([CH3:7])[C:3]1=[S:8].[Cl:9][CH2:10][C:11](=[O:14])[CH2:12]Cl>CC(C)=O>[Cl-:9].[CH3:1][NH+:2]1[CH:6]=[CH:5][N:4]([CH3:7])[CH:3]1[S:8][CH2:12][C:11](=[O:14])[CH2:10][Cl:9]

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 260361,3-Dimethyl-2-imidazolidinethione

Product 1

HCID 867448171,3-dimethyl-2-[(3-chloro-2-oxopropyl)thio]-1H-imidazolium chlorideYield 173.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 1.01 g (0.0079 mol) of 1,3-dimethylimidazolin-2-thione (prepared by the procedure Of B.L. Benac et al, Org. Syn. 64, 92 (1985) in 40 mL of acetone was added dropwise to a solution of 1.0 g (0.0079 mol) of 1,3-dichloropropanone in 50 mL of acetone over 2 hours. The resulting solution was stirred at room temperature for 18 hours whereupon a precipitate formed. The latter was removed by filtration and dried to obtain 1.76 g (87%) of 1,3-dimethyl-2-[(3-chloro-2-oxopropyl)thio]-1H-imidazolium chloride, m.p. 157-158° C.

Workup

  1. customformed
  2. customThe latter was removed by filtration
  3. customdried

Sources & evidence

ORD record
ord-a47a9a76ded74dc98a780beb8d0544e6
Source dataset
uspto-grants-1991_06
Patent number
US05021440

Reaction notes

Loading…