2-Aminothiophenol → 2-(3-(Benzo[d]thiazol-2-yl)phenoxy)-2-methylpropanoic acid

HRID 1748998Notes

Reaction equation

HRID 1748998 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[O:6][C:7]([CH3:14])([CH3:13])[C:8]([O:10]CC)=[O:9])=O.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[SH:25].[OH-].[Na+]>CO>[S:25]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[C:1]1[C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[O:6][C:7]([CH3:13])([CH3:14])[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 87132-AminothiophenolHCID 14798Sodium HydroxideHCID 18766496Ethyl 2-(3-formylphenoxy)-2-methylpropanoate

Product 1

HCID 682792962-(3-(Benzo[d]thiazol-2-yl)phenoxy)-2-methylpropanoic acidYield 67.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a methanol solvent, a solution including Compound 97b (1.0 eq.) and 2-aminothiophenol (1.0 eq.) was stirred at room temperature for 22 hours. After methanol was evaporated, the residual was purified by silica gel column chromatography using hexane and ethyl acetate (14:1) as a developer. The obtained product was dissolved with 1,4-dioxane, and then, 1 N NaOH (1.5 eq.) was added thereto. The reaction mixture was stirred at room temperature for 17 hours, and 1,4-dioxane was evaporated. The reaction mixture was stirred at room temperature for 17 hours, and 1,4-dioxane was evaporated therefrom. The residual was distributed between ethyl acetate and water, an aqueous layer was acidified with 6 N HCl. The produced precipitate was filtered and washed with water to obtain Compound 120.

Workup

  1. customAfter methanol was evaporated
  2. customthe residual was purified by silica gel column chromatography
  3. dissolutionThe obtained product was dissolved with 1,4-dioxane
  4. stirringThe reaction mixture was stirred at room temperature for 17 hours
  5. custom1,4-dioxane was evaporated
  6. stirringThe reaction mixture was stirred at room temperature for 17 hours
  7. custom1,4-dioxane was evaporated
  8. filtrationThe produced precipitate was filtered
  9. washwashed with water

Sources & evidence

ORD record
ord-0893179ebb1f423a8084b94bb86faae8
Source dataset
uspto-grants-2015_10
Patent number
US09155690B2

Reaction notes

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