2-Aminothiophenol → HCID 22010588, compound

HRID 323130Notes

Reaction equation

HRID 323130 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[H-].[Na+].Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C)C=O.C(OCC)(=O)C>[CH2:20]([O:19][C:17]([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH2:1])=[O:18])[CH3:21]

Participants

6

Reactant 3

HCID 87132-AminothiophenolHCID 24758Sodium hydrideHCID 117544Ethyl 6-bromohexanoate

Product 1

HCID 22010588HCID 22010588, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice bath cooled solution of 2-aminothiophenol (1.80 g) in N,N-dimethylformamide (35 ml) was added sodium hydride (60% in oil, 575 mg). After being stirred in an ice bath for 30 minutes, ethyl 6-bromohexanoate (3.21 g) was added and the mixture was stirred at ambient temperature for 3 hours. The mixture was diluted with ethyl acetate (100 ml) and the solution was washed with water and brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo to give an oil. The oil was purified by silica gel column (1% methanol in chloroform) to give 2-(5-ethoxycarbonylpent-1-yl)thioaniline (3.20 g) as a pale yellow amorphous.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 3 hours
  2. washthe solution was washed with water and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customto give an oil
  6. customThe oil was purified by silica gel column (1% methanol in chloroform)

Sources & evidence

ORD record
ord-7fc7bea4418e45e5a4353649551ab6fa
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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