Hydrochloric Acid → 2-Naphthalenemethanethiol

HRID 358814Notes

Reaction equation

HRID 358814 reaction equation
N[C:2](N)=[S:3].BrC[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1.[OH-].[K+].Cl>C(O)C.O>[SH:3][CH2:2][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 703202-BromomethylnaphthaleneHCID 2723790Thiourea

Product 1

HCID 53142682-NaphthalenemethanethiolYield 91.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Utilizing the procedure of G. G. Urquhart, J. W. Gates and R. Conner, Org. Syn. Coll. Vol. 3, p. 363, thiourea (6.89 g, 90.5 mmol) was added to a solution of 2-(bromomethyl)naphthalene (20.6 g, 90.5 mmol) in anhydrous ethanol (100 mL) and then heated at reflux. After 17 h, the reaction solution was concentrated to an oil. The oil was dissolved in a solution of potassium hydroxide (11.2 g, 199 mmol) in water (100 mL) and heated at reflux for 2 h. The solution was then cooled to 25° C. and treated with aqueous hydrochloric acid (2.0N). The resulting aqueous mixture was extracted with ethyl acetate (3×). The combined ethyl acetate extracts were dried over magnesium sulfate, filtered and evaporated to give yellow crystals (14.5 g, 91.9% yield).

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. concentrationthe reaction solution was concentrated to an oil
  4. temperatureheated
  5. temperatureat reflux for 2 h
  6. extractionThe resulting aqueous mixture was extracted with ethyl acetate (3×)
  7. dry with materialThe combined ethyl acetate extracts were dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-9b244d4e5c824dc499292060f273490d
Source dataset
uspto-grants-1991_03
Patent number
US04997948

Reaction notes

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