Sodium Hydroxide → HCID 57732261, compound

HRID 1808196Notes

Reaction equation

HRID 1808196 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]([F:21])[CH:12]=2)(=[O:10])=[O:9])=[N:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1>[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]([F:21])[CH:12]=2)(=[O:10])=[O:9])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57731924HCID 57731924, compound

Product 1

HCID 57732261HCID 57732261, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 4-{[(5-chloro-1,3-thiazol-2-yl)amino]sulfonyl}-2-fluorobenzoate (Preparation 32, 3.6 g, 10.26 mmol, 1 eq) was suspended in 2.5M sodium hydroxide (16.5 ml, 41 mmol, 4 eq) and dioxane (4 ml) and the reaction mixture heated at 50° C. for 2 hours. The organic solvent was removed in vacuo and the residue diluted with ethyl acetate (20 ml). The remaining solid was removed by filtration and the organic layer separated. The aqueous phase was acidified with concentrated HCl, extracted into ethyl acetate, washed with brine, dried over magnesium sulphate, filtered and evaporated in vacuo. The title compound was obtained as a white solid (2.74 g, 8.1 mmol, 79%).

Workup

  1. customThe organic solvent was removed in vacuo
  2. additionthe residue diluted with ethyl acetate (20 ml)
  3. customThe remaining solid was removed by filtration
  4. customthe organic layer separated
  5. extractionextracted into ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-ed85776b12a64818865635f9599f143d
Source dataset
uspto-grants-2013_01
Patent number
US08357711B2

Reaction notes

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