Sodium Hydroxide → (4-(6-Chloro-2-benzothiazolyl)amino-3-chlorophenyl)acetic acid

HRID 1372677

Reaction equation

HRID 1372677 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19]C)=[O:18])=[CH:12][C:11]=3[Cl:21])[S:8][C:4]=2[CH:3]=1.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=[O:18])=[CH:12][C:11]=3[Cl:21])[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58778710Methyl (4-(6-chloro-2-benzothiazolyl)amino-3-chlorophenyl)acetate

Product 1

HCID 17859264(4-(6-Chloro-2-benzothiazolyl)amino-3-chlorophenyl)acetic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl (4-(6-chloro-2-benzothiazolyl)amino-3-chlorophenyl)acetate (271 mg, 0.74 mmol) was dissolved in THF (4.5 ml). To the resulting solution was added 0.5N NaOH (4.5 ml, 2.25 mmol), followed by stirring at room temperature for 15 hours. The reaction 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 (4-(6-chloro-2-benzothiazolyl)amino-3-chlorophenyl)acetic acid (248 mg, 95%) 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-58fdca4463604b758be4983dfb04ed57
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Linked notes

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