2-Bromopyridine → 4,5-Bis(4-methoxyphenyl)-2-(2-pyridylthio)imidazole

HRID 370758Notes

Reaction equation

HRID 370758 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([SH:22])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[H-].[Na+].Br[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1>CN(C)C=O>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]=[C:11]([S:22][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[NH:10][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 24758Sodium hydrideHCID 178489021HCID 178489021, compound

Product 1

HCID 128323904,5-Bis(4-methoxyphenyl)-2-(2-pyridylthio)imidazoleYield 75.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3.12 g of 4,5-bis(4-methoxyphenyl)-2-mercaptoimidazole is dissolved in 50 ml of absolute dimethylformamide and combined with 0.3 g of sodium hydride (80% strength in white oil). The mixture is stirred for 30 minutes, and then 1.74 g of 2-bromopyridine in 25 ml of dimethylformamide is added dropwise thereto. The reaction mixture is stirred at room temperature under argon for 30 hours. Then the solution is poured into 300 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 methylene chloride/ether, thus obtaining 2.94 g of 4,5-bis(4-methoxyphenyl)-2-(2-pyridylthio)imidazole, mp 94°.

Workup

  1. stirringThe reaction mixture is stirred at room temperature under argon for 30 hours
  2. extractionthe product is extracted with ethyl acetate
  3. dry with materialthe organic solution is dried over sodium sulfate
  4. concentrationconcentrated to dryness under vacuum
  5. customThe residue is recrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-93bd21c76a0746d79e7d147a9e37727b
Source dataset
uspto-grants-1985_07
Patent number
US04528298

Reaction notes

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