Acetic Acid → HCID 12832297, compound

HRID 370760Notes

Reaction equation

HRID 370760 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([S:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N+:29]([O-])=O)[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.O.[C:33](O)(=[O:35])[CH3:34]>C(OC(=O)C)(=O)C.[Fe]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([S:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[NH:29][C:33](=[O:35])[CH3:34])[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

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 12832296HCID 12832296, compound

Product 1

HCID 12832297HCID 12832297, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

At room temperature, 2.5 g of iron filings is added to a solution of 4.34 g of 4,5-bis(4-methoxyphenyl)-2-(2-nitrophenylthio)imidazole in 50 ml of glacial acetic acid and 3 ml of acetic anhydride. The mixture is stirred overnight, poured into 500 ml of water, the precipitated product is vacuum-filtered, taken up in ethyl acetate, and the solution washed with sodium bicarbonate solution. The solution is then dried over sodium sulfate and concentrated to dryness under vacuum. The residue is crystallized from ethyl acetate/ether. Recrystallization from ethyl acetate yields 3.67 g of 4,5-bis(4-methoxyphenyl)-2-(2-acetamidophenylthio)imidazole, mp 183°.

Workup

  1. filtrationthe precipitated product is vacuum-filtered
  2. washthe solution washed with sodium bicarbonate solution
  3. dry with materialThe solution is then dried over sodium sulfate
  4. concentrationconcentrated to dryness under vacuum
  5. customThe residue is crystallized from ethyl acetate/ether
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-370c6538efa641ac84d579e35a92145f
Source dataset
uspto-grants-1985_07
Patent number
US04528298

Reaction notes

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