Hydrochloric Acid → 5-Chloro-3-(3,5-dimethylphenylsulfonyl)indole-2-carboxylic acid

HRID 50035Notes

Reaction equation

HRID 50035 reaction equation
[OH2:1].[OH-:2].[Li+].[Cl:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]([O:16]C)=[O:15])=[C:8]2[S:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[CH:20]=1.Cl>O1CCCC1.O>[Cl:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]([OH:16])=[O:15])=[C:8]2[S:18]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[CH:20]=1)(=[O:2])=[O:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 11727682Methyl 5-chloro-3-(3,5-dimethylphenylthio)indole-2-carboxylate

Product 1

HCID 113719555-Chloro-3-(3,5-dimethylphenylsulfonyl)indole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (0.33 g, 0.0079 mol) was added to a solution of methyl 5-chloro-3-(3,5-dimethylphenylthio)indole-2-carboxylate (1.0 g, 0.0026 mol) in tetrahydrofuran (30 mL) and water (30 mL), then reaction was stirred at room temperature for 4 days. After dilution with water the mixture was acidified with 1N HCl and extracted with ethyl acetate. Organic reaction was washed with brine and dried. Evaporation of the solvent furnished 0.94 (100%) of title compound, mp 277-278° C. (from ethanol).

Workup

  1. customreaction
  2. extractionextracted with ethyl acetate
  3. customOrganic reaction
  4. washwas washed with brine
  5. customdried
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-151f78a6f9304158948cef2c4903e3d9
Source dataset
uspto-grants-2004_03
Patent number
US06710068B2

Reaction notes

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