Thionyl Chloride → HCID 22130786, compound

HRID 1416027Notes

Reaction equation

HRID 1416027 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, compound

Conditions

Temperature
70 °C

Procedure

To 19 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)to

Sources & evidence

ORD record
ord-60d7aa2f87284365945b2bf0766601bc
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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