4-Aminothiophenol → HCID 69522114, compound

HRID 856734Notes

Reaction equation

HRID 856734 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-].[Na+].CC1C=CC(S(O[CH2:22][CH2:23][N:24]2[CH:28]=[CH:27][N:26]=[C:25]2[CH2:29][CH2:30][CH3:31])(=O)=O)=CC=1>CO>[CH2:29]([C:25]1[N:24]([CH2:23][CH2:22][S:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[CH:28]=[CH:27][N:26]=1)[CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 145104-AminothiophenolHCID 14798Sodium HydroxideHCID 22938765HCID 22938765, compound

Product 1

HCID 69522114HCID 69522114, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-aminothiophenol (1.0 g) was dissolved in methanol (20 ml), 3N sodium hydroxide (8.0 ml) was added to the mixture, and 2-(2-propylimidazol-1-yl)ethyl 4-methylbenzene sulfonate (3.7 g) was added to the mixture. The mixture was stirred for 20 hours at room temperature, and the solvent was removed under reduced pressure. Water was added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/ethanol=15/1→6/1), to give 4-[[2-(2-propylimidazol-1-yl)ethyl]sulfanyl]aniline (1.2 g).

Workup

  1. additionwas added to the mixture
  2. customthe solvent was removed under reduced pressure
  3. additionWater was added to the obtained residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/ethanol=15/1→6/1)

Sources & evidence

ORD record
ord-51c4acf4c02a4dac956ed60585f1c268
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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