Potassium Hydroxide → N-[6-chloro-2-(3-chlorobenzoyl)-1H-indol-3-yl]methanesulfonamide

HRID 651028Notes

Reaction equation

HRID 651028 reaction equation
[CH3:1][S:2]([N:5](S(C)(=O)=O)[C:6]1[C:14]2[C:9](=[CH:10][C:11]([Cl:15])=[CH:12][CH:13]=2)[N:8](C(OCC)=O)[C:7]=1[C:21](=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)(=[O:4])=[O:3].[OH-].[K+]>C(O)C.O>[Cl:15][C:11]1[CH:10]=[C:9]2[C:14]([C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[C:7]([C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[NH:8]2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 21710894Ethyl 3-[bis(methylsulfonyl)amino]-6-chloro-2-(3-chlorobenzoyl)-1H-indole-1-carboxylate

Product 1

HCID 9821369N-[6-chloro-2-(3-chlorobenzoyl)-1H-indol-3-yl]methanesulfonamideYield 48%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of the ethyl 3-[bis(methylsulfonyl)amino]-6-chloro-2-(3-chlorobenzoyl)-1H-indole-1-carboxylate (step 1, 532 mg, 0.998 mmol) in ethanol (15 ml) was added a solution of potassium hydroxide (395 mg, 5.99 mmol) in water (8 ml) at room temperature. After stirring for 1 h at ambient temperature, the mixture was concentrated to ca. 10 ml, and partioned between with ethyl acetate (150 ml) and water (100 ml). The organic layer was separated and washed with water (100 ml), and dried (Na2SO4). Removal of the solvent by evaporation gave an crystalline residue, which was crystallized from ethanol/hexane to afford 182 mg (48%) of the title compound.

Workup

  1. concentrationthe mixture was concentrated to ca. 10 ml
  2. customThe organic layer was separated
  3. washwashed with water (100 ml)
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent
  6. customby evaporation
  7. customgave an crystalline residue, which
  8. customwas crystallized from ethanol/hexane

Sources & evidence

ORD record
ord-db66296fe4684e5f99d2e12765540367
Source dataset
uspto-grants-2001_08
Patent number
US06277878B1

Reaction notes

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