Sodium hydride → 4,5-Bis(4-methoxyphenyl)-2-(2-pyrimidylthio)imidazole

HRID 370759Notes

Reaction equation

HRID 370759 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+].Cl[C:26]1[N:31]=[CH:30][CH:29]=[CH:28][N:27]=1>CN(C)C=O.[Cu]>[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[N: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

6

Reactant 3

HCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 178489021HCID 178489021, compound

Product 1

HCID 128322954,5-Bis(4-methoxyphenyl)-2-(2-pyrimidylthio)imidazoleYield 73.6%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 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 1.26 g of 2-chloropyrimidine in 25 ml of dimethylformamide is added dropwise thereto. The reaction mixture is combined with a pinch of powdered copper and stirred for one week under argon at room temperature. The solution is then 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 glacial acetic acid/ether, thus obtaining 2.87 g of 4,5-bis(4-methoxyphenyl)-2-(2-pyrimidylthio)imidazole, mp 86°.

Workup

  1. stirringstirred for one week under argon at room temperature
  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 glacial acetic acid/ether

Sources & evidence

ORD record
ord-41ec407797b748c196fb05b036efbb87
Source dataset
uspto-grants-1985_07
Patent number
US04528298

Reaction notes

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