Hydrochloric Acid → N-(3-Pyrrolidin-3-yl-phenyl)-4-trifluoromethoxy-benzenesulfonamide

HRID 1260226Notes

Reaction equation

HRID 1260226 reaction equation
COC([N:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:11]=2)[CH2:6]1)=O.Cl>CCO>[NH:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[C:12]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:28])[F:29])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:13]=[CH:14][CH:15]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 574944463-[3-(4-Trifluoromethoxy-benzenesulfonylamino)-phenyl]-pyrrolidine-1-carboxylic acid methyl ester

Product 1

HCID 60205208N-(3-Pyrrolidin-3-yl-phenyl)-4-trifluoromethoxy-benzenesulfonamideYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-[3-(4-Trifluoromethoxy-benzenesulfonylamino)-phenyl]-pyrrolidine-1-carboxylic acid methyl ester (500 mg, 1.13 mmol) and HCl (8M, 137.82 mmol) in EtOH (10 ml) were heated under reflux for 48 h. The mixture was extracted twice with ethyl acetate and then NaOH (2M) was added. The aqueous phase was extracted twice with ethyl acetate. The combined organic layers were washed with water and saturated sodium chloride solution, dried over MgSO4 and evaporated under reduced pressure to give the product as a brown oil (200 mg, 46%).

Workup

  1. temperatureunder reflux for 48 h
  2. extractionThe mixture was extracted twice with ethyl acetate
  3. additionNaOH (2M) was added
  4. extractionThe aqueous phase was extracted twice with ethyl acetate
  5. washThe combined organic layers were washed with water and saturated sodium chloride solution
  6. dry with materialdried over MgSO4
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b66e5f571bdf4dd7954e8758c6a5cf3b
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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