Hydrochloric Acid → 1-(Cyclohexylmethyl)-N-cyclopropyl-2-methyl-1H-pyrrole-3-sulfonamide

HRID 1844709Notes

Reaction equation

HRID 1844709 reaction equation
[CH:1]1([CH2:7][N:8]2[C:12]([CH3:13])=[C:11]([S:14](=[O:20])(=[O:19])[NH:15][CH:16]3[CH2:18][CH2:17]3)[CH:10]=[C:9]2C(O)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>CCO>[CH:1]1([CH2:7][N:8]2[CH:9]=[CH:10][C:11]([S:14]([NH:15][CH:16]3[CH2:18][CH2:17]3)(=[O:20])=[O:19])=[C:12]2[CH3:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 708691941-(Cyclohexylmethyl)-4-(N-cyclopropylsulfamoyl)-5-methyl-1H-pyrrole-2-carboxylic acid

Product 1

HCID 708690871-(Cyclohexylmethyl)-N-cyclopropyl-2-methyl-1H-pyrrole-3-sulfonamideYield 61.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of compound 3b (6.0 g, 17.6 mmol) in EtOH (100 mL) was added 4N aq. HCl (50 mL) and the solution was refluxed for 5 h, cooled to rt and concentrated. The residue was diluted with EA, washed with brine, dried over Na2SO4, filtered, concentrated and purified by CC (EA/PE=1/5) to give compound 3c (3.2 g, 61%) as a white solid.

Workup

  1. temperaturethe solution was refluxed for 5 h
  2. concentrationconcentrated
  3. additionThe residue was diluted with EA
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by CC (EA/PE=1/5)

Sources & evidence

ORD record
ord-414a83c1c54e4fe5b14cbf0905802be4
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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