Hydrochloric Acid → HCID 42629164, compound

HRID 1616094Notes

Reaction equation

HRID 1616094 reaction equation
[NH:1]([C:5]1[C:6]([F:13])=[CH:7][C:8]([CH3:12])=[C:9]([SH:11])[CH:10]=1)C(C)=O.[OH-].[K+].Cl>O>[NH2:1][C:5]1[C:6]([F:13])=[CH:7][C:8]([CH3:12])=[C:9]([SH:11])[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66776531HCID 66776531, compound

Product 1

HCID 42629164HCID 42629164, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Crude 5-acetamino-4-fluoro-2-methyl-benzenethiol (280 g, 1.41 mol) was added to a 5% (w/w) solution of potassium hydroxide (250 g, 4.46 mol) in water and the mixture was refluxed for 5 hours. The resulting solution was adjusted to pH 7 with dilute hydrochloric acid and was then extracted with ethyl acetate. The organic phase was dried with sodium sulfate and concentrated under reduced pressure to give 5-amino-4-fluoro-2-methyl-benzenethiol as a crude intermediate (160 g, 88%).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-51edb68047fc4a50af2988f84a844a9e
Source dataset
uspto-grants-2014_07
Patent number
US08765774B2

Reaction notes

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