Sodium Hydroxide → (3-Chloro-4-(6-fluoro-2-benzothiazolyl)aminophenyl)acetic acid

HRID 1372673Notes

Reaction equation

HRID 1372673 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:19][C:20]([O:22]C)=[O:21])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:12]=2[N:13]=1.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:19][C:20]([OH:22])=[O:21])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58778884Methyl (3-chloro-4-(6-fluoro-2-benzothiazolyl)aminophenyl)acetate

Product 1

HCID 17859168(3-Chloro-4-(6-fluoro-2-benzothiazolyl)aminophenyl)acetic acidYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl (3-chloro-4-(6-fluoro-2-benzothiazolyl)aminophenyl)acetate (158 mg, 0.45 mmol) was dissolved in THF (3 ml). To the resulting solution was added 0.5N NaOH (3.0 ml, 1.50 mmol), and the resulting mixture was stirred at room temperature for 18 hours. The mixture was poured in ice-1N HCl. The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give (3-chloro-4-(6-fluoro-2-benzothiazolyl)aminophenyl)acetic acid (127 mg, 84%) as a pale yellow solid.

Workup

  1. customThe crystals thus precipitated
  2. filtrationwere collected by filtration under reduced pressure
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-60662585a9744974962dc060f19ae21a
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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