Aniline → HCID 12832306, compound

HRID 1995197Notes

Reaction equation

HRID 1995197 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N([O-])=O.[Na+].C([O-])(=O)C.[Na+].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:26]=[C:27]([SH:38])[NH:28][C:29]=2[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[CH:21][CH:20]=1.[OH-].[Na+]>S(=O)(=O)(O)O.O.CN(C)C=O.C(Cl)Cl.[Cu]>[CH3:37][O:36][C:33]1[CH:34]=[CH:35][C:30]([C:29]2[N:28]=[C:27]([S:38][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[NH:26][C:25]=2[C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)=[CH:31][CH:32]=1

Participants

11

Reactant 5

HCID 6115AnilineHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 178489021HCID 178489021, compound

Product 1

HCID 12832306HCID 12832306, compoundYield 39.6%

Reagents, catalysts & solvents 5

HCID 23978CopperCatalystHCID 962WaterSolvent4×HCID 1118Sulfuric AcidSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1.5 g of aniline is dissolved in 2.0 g of concentrated sulfuric acid and 30 ml of water and, after the addition of 10 g of ice, diazotized at 0° with a solution of 1.2 g of sodium nitrite in 10 ml of water. The diazonium salt solution is then neutralized with sodium acetate and introduced at 5° under thorough agitation into a solution of 5.02 g of 4,5-bis(4-methoxyphenyl)-2-mercaptoimidazole in 200 ml of dimethylformamide containing 10 ml of water, 1.93 g of sodium hydroxide solution, as well as 1.15 g of powdered copper. The mixture is further stirred for 20 minutes, poured into 600 ml of water, the thus-precipitated oil is taken up in methylene chloride, the organic solution is washed with water, dried over sodium sulfate, and concentrated to dryness under vacuum. The residue is chromatographed on 200 g of silica gel. Elution with acetone/hexane 2:3 yields 2.47 g of 4,5-bis(4 -methoxyphenyl)-2-(phenylthio)imidazole, mp 177°-179° after recrystallization from hexane/ethyl acetate.

Workup

  1. washthe organic solution is washed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness under vacuum
  4. customThe residue is chromatographed on 200 g of silica gel
  5. washElution with acetone/hexane 2:3

Sources & evidence

ORD record
ord-670b294202504b20857ffe5d423e6f62
Source dataset
uspto-grants-1983_09
Patent number
US04402960

Reaction notes

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