Potassium Hydroxide → 5-(Cyclohexylmethyl)-1-methyl-1H-pyrrole-2-sulfonamide

HRID 1844738Notes

Reaction equation

HRID 1844738 reaction equation
[CH:1]1([C:7]([C:9]2[N:13]([CH3:14])[C:12]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.NN.O.[OH-].[K+]>C(O)COCCO.O>[CH:1]1([CH2:7][C:9]2[N:13]([CH3:14])[C:12]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 708743255-(Cyclohexanecarbonyl)-1-methyl-1H-pyrrole-2-sulfonamide

Product 1

HCID 708740515-(Cyclohexylmethyl)-1-methyl-1H-pyrrole-2-sulfonamideYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Procedure

To a solution of compound 25d (1.1 g, 4.1 mmol) in diethylene glycol (50 mL) was added NH2NH2.H2O (0.28 g, 4.5 mmol). The mixture was refluxed for 2 h and then the water and excess NH2NH2.H2O was removed under vacuum. Then KOH (0.46 g, 8.2 mmol) was added and the mixture was refluxed for 4 h, cooled, diluted with water and extracted with EA. The combined organic layers were washed with brine, dried over Na2SO4, evaporated and purified by prep-TLC to give compound 25e (462 mg, 46%).

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customthe water and excess NH2NH2.H2O was removed under vacuum
  3. temperaturethe mixture was refluxed for 4 h
  4. temperaturecooled
  5. extractionextracted with EA
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. custompurified by prep-TLC

Sources & evidence

ORD record
ord-2d9bb8f1d70843689a3490e7fc24ae8c
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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