Hydrochloric Acid → HCID 89537957, compound

HRID 1774100Notes

Reaction equation

HRID 1774100 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:18][CH3:19])[C:5]([NH:11]C(=O)C(F)(F)F)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].O.[OH-].[Li+].Cl>CO.O>[NH2:11][C:5]1[C:4]([S:18][CH3:19])=[CH:3][C:2]([CH3:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 89536745HCID 89536745, compound

Product 1

HCID 89537957HCID 89537957, compoundYield 101.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

22.0 g (75.0 mmol) of 5-methyl-3-(methylthio)-2-(trifluoroacetylamino)benzoic acid and 9.44 g (225 mmol) of lithium hydroxide monohydrate were heated under reflux in a mixture of 200 ml of methanol and 30 ml of water for 4 h. For work-up, the contents were cooled and freed of the solvents. The residue was taken up in water and the mixture was acidified to pH<3 with dilute hydrochloric acid. The mixture was stirred at a temperature of 0° C.-5° C. for 30 minutes and then filtered. 15.0 g of 2-amino-5-methyl-3-(methylthio)benzoic acid of a purity of >95% by weight were obtained as residue.

Workup

  1. temperatureFor work-up, the contents were cooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-dacdbb42c714462ca292ff49678947e9
Source dataset
uspto-grants-2016_02
Patent number
US09259001B2

Reaction notes

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