Ethanethiol → HCID 178477296, compound

HRID 1633423Notes

Reaction equation

HRID 1633423 reaction equation
[CH3:1][N:2]=[C:3]([OH:19])[C:4]1[C:5](=[C:9]([N+]([O-])=O)[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:6]([OH:8])=[O:7].[CH2:20]([SH:22])[CH3:21].C([O-])(=O)C.[Na+]>C(OCC)(=O)C>[CH3:1][N:2]=[C:3]([OH:19])[C:4]1[C:5](=[C:9]([S:22][CH2:20][CH3:21])[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 517045Sodium AcetateHCID 178485491HCID 178485491, compound

Product 1

HCID 178477296HCID 178477296, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5.02 g (20 mmols) of 3,5-dinitrophthalic acid N-methylimide, 2.73 g (44 mmols) of ethylmercaptan, 8.2 g (1 0 mmols) of anhydrous sodium acetate and 50 ml of ethyl acetate are kept at 25° C. overnight and then kept under reflux, again overnight. The reaction mixture is evaporated, the residue is taken up in methylene chloride/water, the extracts are washed with saturated NaHCO3 solution, dried over sodium sulfate and evaporated and the residue is chromatographed with methylene chloride over 20 g of silica gel. After recrystallisation from methylene chloride/n-pentane, 2.40 g (45% of theory) of 3-ethylthio-5-nitrophthalic acid N-methylimide, with a melting point of 193°-4° C., are obtained.

Workup

  1. temperatureunder reflux, again overnight
  2. customThe reaction mixture is evaporated
  3. washthe extracts are washed with saturated NaHCO3 solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customthe residue is chromatographed with methylene chloride over 20 g of silica gel
  7. customAfter recrystallisation from methylene chloride/n-pentane, 2.40 g (45% of theory) of 3-ethylthio-5-nitrophthalic acid N-methylimide
  8. customwith a melting point of 193°-4° C., are obtained

Sources & evidence

ORD record
ord-55661acaf59b4bdd914b876877a43d07
Source dataset
uspto-grants-1984_10
Patent number
US04480105

Reaction notes

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