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

HRID 1372675

Reaction equation

HRID 1372675 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]([CH3:18])[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]([CH3:18])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58778443Methyl (3-chloro-4-(6-methyl-2-benzothiazolyl)aminophenyl)acetate

Product 1

HCID 17858843(3-Chloro-4-(6-methyl-2-benzothiazolyl)aminophenyl)acetic acidYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl (3-chloro-4-(6-methyl-2-benzothiazolyl)aminophenyl)acetate (274 mg, 0.79 mmol) was dissolved in THF (5 ml). To the resulting solution was added 0.5N NaOH (5.0 ml, 2.50 mmol), followed by stirring at room temperature for 15 hours. The reaction mixture was poured in ice-1N HCR. 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-methyl-2-benzothiazolyl)aminophenyl)acetic acid (202 mg, 77%) 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-53a24afdd19748c783a8fbeaf88056cd
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Linked notes

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