Chloroacetone → HCID 15165836, compound

HRID 2372282Notes

Reaction equation

HRID 2372282 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[SH:13].C(N(CC)CC)C.Cl[CH2:22][C:23](=[O:25])[CH3:24]>CC(C)=O>[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][CH2:22][C:23](=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 178479924HCID 178479924, compound

Product 1

HCID 15165836HCID 15165836, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 4.76 g (0.025 mol) of 1-methyl-5-phenyl-imidazol-2-thiol and 3.15 g (0.031 mol) of triethylamine in 250 mL of acetone was added 2.55 g (0.28 mol) of chloroacetone in 250 mL of acetone. The solution was stirred at room temperature for 16 hours. The acetone was removed by evaporation and the residue was partitioned between ethyl acetate and water. The ethyl acetate phase was washed with water, brine, and dried over magnesium sulfate. The solvent was evaporated from the dried solution to obtain as residue 6.16 grams of 1-methyl-5-phenyl-2[(2-oxopropyl)thio]imidazole which was purified by flash chromatography on silica gel using 2 percent methanol in chloroform as eluant.

Workup

  1. customThe acetone was removed by evaporation
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe ethyl acetate phase was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated from the dried solution

Sources & evidence

ORD record
ord-16a6d84f205e415e8a2023e08fbd30b8
Source dataset
uspto-grants-1992_03
Patent number
US05098707

Reaction notes

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