Potassium Hydroxide → HCID 67353505, compound

HRID 2272280Notes

Reaction equation

HRID 2272280 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[CH:23]=[C:22]([N:24](CS(C)(=O)=O)[S:25]([CH3:28])(=[O:27])=[O:26])[C:21]([CH:34]4[CH2:36][CH2:35]4)=[CH:20][C:13]=3[C:14]=2[C:15]([O:17]CC)=[O:16])=[CH:6][CH:5]=1>C(O)C.O>[CH:34]1([C:21]2[C:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][C:12]3[O:11][C:10]([C:7]4[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=4)=[C:14]([C:15]([OH:17])=[O:16])[C:13]=3[CH:20]=2)[CH2:35][CH2:36]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67352915HCID 67352915, compound

Product 1

HCID 67353505HCID 67353505, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (15.1 g, 270 mmol) was added to a solution of the ethyl 2-(4-chlorophenyl)-5-cyclopropyl-6-(N-(methylsulfonylmethyl)methylsulfonamido)benzofuran-3-carboxylate in ethanol (64 mL) and water (32 mL) under nitrogen atmosphere. The reaction was refluxed for 1 hour and then concentrated in vacuo. The remaining solid was dissolved in water and the solution was acidified with 1N HCl (250 mL) until a precipitate formed. The solid was filtered and then dried to afford 5-cyclopropyl-2-(4-chlorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylic acid (8.7 g, quantitative yield).

Workup

  1. temperatureThe reaction was refluxed for 1 hour
  2. concentrationconcentrated in vacuo
  3. dissolutionThe remaining solid was dissolved in water
  4. customformed
  5. filtrationThe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-c533390ce37145f1a654f984852c19f5
Source dataset
uspto-grants-2015_09
Patent number
US09119868B2

Reaction notes

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