Dichloromethane → HCID 67915249, compound

HRID 1086497Notes

Reaction equation

HRID 1086497 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][N:4]=[C:3]1[S:13][CH2:14][C:15](=[O:17])[CH3:16].F[C:19](F)(F)S(OC)(=O)=O.C(Cl)[Cl:28]>C(OCC)(=O)C>[Cl-:28].[CH3:19][NH+:4]1[CH:5]=[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:2]([CH3:1])[CH:3]1[S:13][CH2:14][C:15](=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9526Methyl triflateHCID 15165836HCID 15165836, compound

Product 1

HCID 67915249HCID 67915249, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0 25 gram (0.001 mol) of the 1-methyl-5-phenyl-2[(2-oxopropyl)thio]imidazole, prepared as above described, in 10 mL of methylene chloride was added 0.164 g (0.001 mol) of methyl trifluoromethanesulfonate, and the solution was stirred overnight at room temperature. The solvent was evaporated and the residue was converted to the chloride ion form by dissolving in 20% methanol/water and passing through Dowex-1 (Cl-)ion exchange column. The column was eluted with 20 percent methanol in water and the eluate subjected to reduced pressure to evaporate the solvent and to obtain a residue. The residue was stirred overnight in ethyl acetate, filtered and recrystallized from isopropanol/hexane to obtain purified 1,3 dimethyl 4-phenyl-2-[(2-oxopropyl)thio]-1H-imidazolium chloride, m.p. 143°-146° C.

Workup

  1. customThe solvent was evaporated
  2. dissolutionby dissolving in 20% methanol/water
  3. washThe column was eluted with 20 percent methanol in water
  4. customto evaporate the solvent
  5. customto obtain a residue
  6. filtrationfiltered
  7. customrecrystallized from isopropanol/hexane
  8. customto obtain
  9. custompurified 1,3 dimethyl 4-phenyl-2-[(2-oxopropyl)thio]-1H-imidazolium chloride, m.p. 143°-146° C.

Sources & evidence

ORD record
ord-a72159647e164aa284f528bdc016d963
Source dataset
uspto-grants-1991_07
Patent number
US05030644

Reaction notes

Loading…