Potassium Hydroxide → 3-{[(5-Chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acid

HRID 589677Notes

Reaction equation

HRID 589677 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([S:12]([NH:15][C:16]3[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=3)[C:19]([O:21]C)=[O:20])(=[O:14])=[O:13])=[C:9]([CH3:26])[C:8]=2[CH:27]=1>CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([S:12]([NH:15][C:16]3[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=3)[C:19]([OH:21])=[O:20])(=[O:14])=[O:13])=[C:9]([CH3:26])[C:8]=2[CH:27]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 56941887HCID 56941887, compound

Product 1

HCID 569413063-{[(5-Chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acidYield 94.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

1.7 M aq. KOH (5 mL) was added to a slurry of methyl 3-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoate (400 mg, 1.01 mmol) in MeOH (5 mL). The reaction mixture was stirred at 50° C. for 1.5 h. After removal of the MeOH under reduced pressure, the remaining aqueous solution was acidified to pH 3 by addition of ortho-phosphoric acid. The precipitate was collected, washed with water and dried giving the title compound as an off-white solid (363 mg, 91%). 1H NMR (500 MHz, MeOH-d4) δ ppm 2.49 (s, 3 H) 7.32-7.39 (m, 2 H) 7.46 (dd, J=8.67, 2.08 Hz, 1 H) 7.75 (dt, J=7.32, 1.59 Hz, 1 H) 7.82-7.86 (m, 3 H). MS (ESI+) m/z 399 [M+NH4]+.

Workup

  1. customAfter removal of the MeOH under reduced pressure
  2. additionthe remaining aqueous solution was acidified to pH 3 by addition of ortho-phosphoric acid
  3. customThe precipitate was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-76952c06bb09464f8aa9be1b911e5ff1
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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