2-Aminothiophenol → HCID 19106821, compound

HRID 1197482Notes

Reaction equation

HRID 1197482 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[OH-].[Na+].Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH2:14]>C(O)C>[C:15]1([C:13](=[CH2:12])[CH2:14][S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH2:1])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 87132-AminothiophenolHCID 14798Sodium HydroxideHCID 234998(3-bromoprop-1-en-2-yl)benzene

Product 1

HCID 19106821HCID 19106821, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

The compound, 2-aminothiophenol, (12.5 g) was added to a solution of sodium hydroxide (4.5 g) in ethanol (100 ml) keeping the temperature less than 30° C. Then 1-bromo-2phenyl-2-propene (21 g) was added and the mixture was stirred at 60° C. for 3 h. The precipitated solid was filtered and washed with ethanol. The solvent was removed and the residue was chromatographed on silica gel with hexanes/ethyl acetate (7:1) to yield the title compound (14.5 g). As an oil.

Workup

  1. customthe temperature less than 30° C
  2. filtrationThe precipitated solid was filtered
  3. washwashed with ethanol
  4. customThe solvent was removed
  5. customthe residue was chromatographed on silica gel with hexanes/ethyl acetate (7:1)

Sources & evidence

ORD record
ord-560cbb259f4347eea88862b1489ab87f
Source dataset
uspto-grants-1994_01
Patent number
US05276039

Reaction notes

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