Lithium Hydroxide → 4-{[(5-Chloro-1,3-thiazol-2-yl)amino]sulfonyl}-2-cyanobenzoic acid

HRID 401766Notes

Reaction equation

HRID 401766 reaction equation
[Cl:1][C:2]1[S:6][C:5]([NH:7][S:8]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[C:13]([C:21]#[N:22])[CH:12]=2)(=[O:10])=[O:9])=[N:4][CH:3]=1.[OH-].[Li+]>O1CCOCC1.O>[Cl:1][C:2]1[S:6][C:5]([NH:7][S:8]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([OH:17])=[O:16])=[C:13]([C:21]#[N:22])[CH:12]=2)(=[O:10])=[O:9])=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86630782Methyl 4-{[(5-chloro-1,3-thiazol-2-yl)amino]sulfonyl}-2-cyanobenzoate

Product 1

HCID 866307814-{[(5-Chloro-1,3-thiazol-2-yl)amino]sulfonyl}-2-cyanobenzoic acidYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Methyl 4-{[(5-chloro-1,3-thiazol-2-yl)amino]sulfonyl}-2-cyanobenzoate (Preparation 21, 124 mg, 0.348 mmol, 1 eq) was dissolved in dioxane (2.5 ml): water (2.5 ml), lithium hydroxide (200 mg, 5 mmol, 14 eq) was added and the reaction mixture stirred at room temperature for 1 hour. The reaction mixture was diluted with water (5 ml), washed with ethyl acetate (10 ml), acidified with 2M HCl (10 ml), extracted into ethyl acetate (10 ml), dried over sodium sulphate, filtered and evaporated to yield the title compound as a brown solid (95 mg, 0.27 mmol, 79%).

Workup

  1. washwashed with ethyl acetate (10 ml)
  2. extractionextracted into ethyl acetate (10 ml)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-c73a0c9eee8e4f60941184bfd29e2ebd
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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