2-Iodothiophene → HCID 12832369, compound

HRID 370796Notes

Reaction equation

HRID 370796 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([SH:20])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[H-].[Na+].I[C:24]1[S:25][CH:26]=[CH:27][CH:28]=1>CN(C)C=O>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:11]=[C:10]([S:20][C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)[NH:9][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 189212-IodothiopheneHCID 24758Sodium hydrideHCID 178527835HCID 178527835, compound

Product 1

HCID 12832369HCID 12832369, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6.43 g of 4,5-bis(4-chlorophenyl)-2-mercaptoimidazole is dissolved in 150 ml of absolute dimethylformamide and combined with 0.6 g of sodium hydride (80% strength in white oil). The mixture is agitated for another 30 minutes, and then 4.25 g of 2-iodothiophene in 30 ml of dimethylformamide is added dropwise thereto; the mixture is heated under reflux for 16 hours under argon. The solution is then poured into 600 ml of ice water, the product is extracted with ethyl acetate; the organic solution is dried over sodium sulfate and concentrated to dryness under vacuum. The residue is recrystallized from ether, yielding 7.02 g of 4,5-bis(4-chlorophenyl)-2-(2-thienylthio)imidazole, mp 219°.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 16 hours under argon
  3. extractionthe product is extracted with ethyl acetate
  4. dry with materialthe organic solution is dried over sodium sulfate
  5. concentrationconcentrated to dryness under vacuum
  6. customThe residue is recrystallized from ether

Sources & evidence

ORD record
ord-28157cb581a341df91cb0eb7e7e32769
Source dataset
uspto-grants-1985_07
Patent number
US04528298

Reaction notes

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