3-Fluoroaniline → HCID 12832310, compound

HRID 370771Notes

Reaction equation

HRID 370771 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)N.N([O-])=O.[Na+].C([O-])(=O)C.[Na+].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:27]=[C:28]([SH:39])[NH:29][C:30]=2[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[CH:22][CH:21]=1>S(=O)(=O)(O)O.O.CN(C)C=O>[CH3:38][O:37][C:34]1[CH:35]=[CH:36][C:31]([C:30]2[N:29]=[C:28]([S:39][C:4]3[CH:6]=[CH:7][CH:8]=[C:2]([F:1])[CH:3]=3)[NH:27][C:26]=2[C:23]2[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)=[CH:32][CH:33]=1

Participants

8

Reactant 4

HCID 97423-FluoroanilineHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 178489021HCID 178489021, compound

Product 1

HCID 12832310HCID 12832310, compoundYield 36.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 1118Sulfuric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

5.49 g of 3-fluoroaniline is dissolved in 6.0 g of concentrated sulfuric acid and 120 ml of water and, after the addition of 10 g of ice, diazotized at 0° with a solution of 3.6 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 17.2 g of 4,5-bis(4-methoxyphenyl)-2-mercaptoimidazole in 700 ml of dimethylformamide. The mixture is agitated for another 20 minutes, poured into 2.5 l of water, extracted with ethyl acetate, the organic solution washed with water, dried over sodium sulfate, and concentrated to dryness under vacuum. The residue is chromatographed on 500 g of neutral aluminum oxide (activity stage II). Elution with ethyl acetate/hexane produces 7.24 g of 4,5-bis(4-methoxyphenyl)-2-(3-fluorophenylthio)imidazole, mp 147°-149° after recrystallization from ether/ethyl acetate.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic solution washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness under vacuum
  5. customThe residue is chromatographed on 500 g of neutral aluminum oxide (activity stage II)
  6. washElution with ethyl acetate/hexane

Sources & evidence

ORD record
ord-a7fb530eb81042e1ba93271a246f0351
Source dataset
uspto-grants-1985_07
Patent number
US04528298

Reaction notes

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