Hydrochloric Acid → Benzenethiol, 5-amino-2-chloro-4-fluoro-

HRID 6467Notes

Reaction equation

HRID 6467 reaction equation
[NH:1]([C:5]1[C:6]([F:13])=[CH:7][C:8]([Cl:12])=[C:9]([SH:11])[CH:10]=1)C(C)=O.[OH-].[Na+].Cl>O>[NH2:1][C:5]1[C:6]([F:13])=[CH:7][C:8]([Cl:12])=[C:9]([SH:11])[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13488968N-(4-Chloro-2-fluoro-5-sulfanylphenyl)acetamide

Product 1

HCID 11019406Benzenethiol, 5-amino-2-chloro-4-fluoro-Yield 97.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 100 ml reaction flask, 4.8 g (0.022 mol) of 5-acetamino-2-chloro-4-fluoro-thiophenol, 2.55 g (0.064 mol) of sodium hydroxide and 25.5 cc of water were added and stirred under reflux for 4 hours to obtain a uniform solution. The solution was cooled to room temperature and neutralized with 10% hydrochloric acid. The precipitated solid was extracted with 25 cc of ethyl acetate, followed by removal of water and distillation under reduced pressure to obtain 3.8 g of 5-amino-2-chloro-4-fluoro-thiophenol as slightly yellow crystals.

Workup

  1. additionwere added
  2. temperatureunder reflux for 4 hours
  3. customto obtain a uniform solution
  4. extractionThe precipitated solid was extracted with 25 cc of ethyl acetate
  5. customfollowed by removal of water and distillation under reduced pressure

Sources & evidence

ORD record
ord-e9daf0d13fb242e8a2f100e9a0e8682e
Source dataset
uspto-grants-1993_09
Patent number
US05248822

Reaction notes

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