Thiophenol → HCID 178437673, compound

HRID 1728327Notes

Reaction equation

HRID 1728327 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:10][C:11]1[NH:12][C:13](I)=[C:14]([CH2:16][CH3:17])[N:15]=1>CN(C)C=O>[CH3:10][C:11]1[NH:12][C:13]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:14]([CH2:16][CH3:17])[N:15]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 178437672HCID 178437672, compound

Product 1

HCID 178437673HCID 178437673, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 2.24 g of thiophenol (20.3 mmol) in 16 ml of dry dimethylformamide is added 1.4 g of sodium hydride (60% oil suspension: 35 mmol) under ice cooling. Ten minutes later, 3.2 g of 2-methyl-4-ethyl-5-iodoimidazole (13.6 mmol) is added to the mixture, which is heated at 130° C. in a nitrogen atmosphere. Two hours later, the dimethylformamide is evaporated in vacuo. The residue is mixed with dry ice and extracted with methylene chloride. The extract is washed with water, dried over Na2SO4, filtered and the liltrate is concentrated in vacuo. The crude product is chromatographed on a column of silica gel, eluting with 3% methanol/methylene chloride. The product is recrystallized from ethyl acetate/isopropyl ether to give 1.9 g of 2-methyl-4-ethyl-5-phenylthio-imidazole 2. Yield, 64%: mp. 171° C.

Workup

  1. customTwo hours later, the dimethylformamide is evaporated in vacuo
  2. additionThe residue is mixed with dry ice
  3. extractionextracted with methylene chloride
  4. washThe extract is washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe liltrate is concentrated in vacuo
  8. customThe crude product is chromatographed on a column of silica gel
  9. washeluting with 3% methanol/methylene chloride
  10. customThe product is recrystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-27bad5637f464010a09ff0ec31e8893a
Source dataset
uspto-grants-1994_07
Patent number
US05326780

Reaction notes

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