Carbon Disulfide → HCID 178527795, compound

HRID 378861Notes

Reaction equation

HRID 378861 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[C:10](=S)=[S:11].[OH-].[K+]>C(O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[O:9][C:10]([SH:11])=[N:1][C:2]=2[CH:7]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 72652-Amino-4-chlorophenolHCID 14797Potassium Hydroxide

Product 1

HCID 178527795HCID 178527795, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2 g portion of 2-amino-4-chlorophenol was dissolved in 150 ml of ethanol, and the solution was mixed with 80 ml of carbon disulfide and 937 mg of potassium hydroxide and heated under reflux for 8 hours. The solvent was evaporated under a reduced pressure, and the residual oily mixture was mixed with 50 ml of 1 N hydrochloric acid aqueous solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate and then the solvent was evaporated under a reduced pressure. By recrystallizing the thus obtained mixture from ethyl acetate, the title compound (1.3 g) in light yellow color was obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 8 hours
  3. customThe solvent was evaporated under a reduced pressure
  4. additionthe residual oily mixture was mixed with 50 ml of 1 N hydrochloric acid aqueous solution
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried with magnesium sulfate
  8. customthe solvent was evaporated under a reduced pressure
  9. customBy recrystallizing the thus obtained mixture from ethyl acetate

Sources & evidence

ORD record
ord-89c88c3462f64764a9d289380d81b0ce
Source dataset
uspto-grants-2001_10
Patent number
US06297246B1

Reaction notes

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