Thionyl Chloride → HCID 22130786, compound

HRID 1857726Notes

Reaction equation

HRID 1857726 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][N:6]1[C:10]([S:11][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=2)=[C:9]([CH2:20]O)[N:8]=[C:7]1[CH3:22]>>[Cl:3][CH2:20][C:9]1[N:8]=[C:7]([CH3:22])[N:6]([CH3:5])[C:10]=1[S:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 22130478HCID 22130478, compound

Product 1

HCID 22130786HCID 22130786, compoundYield 73%

Conditions

Temperature
70 °C

Procedure

To 1.9 ml of thionyl chloride was added 370 mg (1.4 mmol) of [1,2-dimethyl-5-(3,5-dimethylphenylthio)-1H-imidazol-4-yl]methanol (42b), and the mixture was heated at 70° C. for 3 hours. The reaction mixture was concentrated under reduced pressure. Ice-water and then a saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture to neutralize, and extracted with diethyl ether. The organic layer was washed with water and dried over sodium sulfate, and the solvent was concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate) to give 288 mg of 4-chloromethyl-1,2-dimethyl-5-(3,5-dimethylphenylthio)imidazole (42c) as oil (yield 73%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionIce-water and then a saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-cbec1489483d40ca9a5239a309f4abf0
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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