Hydrochloric Acid → 3-(Benzyloxy)benzene-1-thiol

HRID 1616942Notes

Reaction equation

HRID 1616942 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.N([O-])=O.[Na+].O(CC)C([S-])=[S:23].[K+].[OH-].[K+]>O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([SH:23])[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 928923-BenzyloxyanilineHCID 2735045Potassium ethylxanthateHCID 23668193Sodium Nitrite

Product 1

HCID 249006013-(Benzyloxy)benzene-1-thiol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

3-Benzyloxyaniline (2.06 g, 10.3 mmol) was dissolved in water (40 ml) and concentrated HCl (8 ml). The solution was cooled to 0° C. and solution of sodium nitrite (778 mg, 11.3 mmol) in water (10 ml) was added. After 15 min stirring at 0° C., the mixture was added to a solution of potassium ethyl xanthate (3.1 g, 20 mmol) in water (10 ml), and heated to 65° C. for 30 min. After cooling to room temperature, the reaction mixture was extracted twice with ethyl acetate. The combined organic layers were washed with 1N NaOH and water, and dried over MgSO4. The solvent was evaporated and the residue was dissolved in ethanol (50 ml). Potassium hydroxide (2 g, 40 mmol) was added and the mixture was heated to reflux for 16 h. The reaction mixture was cooled to room temperature, concentrated, and partitioned between diethylether and water. The aqueous layer was acidified to pH 1 with concentrated HCl, and then extracted twice with methylene chloride. The combined organic layers were dried over MgSO4 and the solvent was evaporated. The product was used in the next reaction step without further purification.

Workup

  1. temperatureheated to 65° C. for 30 min
  2. temperatureAfter cooling to room temperature
  3. extractionthe reaction mixture was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed with 1N NaOH and water
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated
  7. dissolutionthe residue was dissolved in ethanol (50 ml)
  8. temperaturethe mixture was heated
  9. temperatureto reflux for 16 h
  10. temperatureThe reaction mixture was cooled to room temperature
  11. concentrationconcentrated
  12. custompartitioned between diethylether and water
  13. extractionextracted twice with methylene chloride
  14. dry with materialThe combined organic layers were dried over MgSO4
  15. customthe solvent was evaporated
  16. customThe product was used in the next reaction step without further purification

Sources & evidence

ORD record
ord-4c9d2d64f19b454c930f3abcff6088ca
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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