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

HRID 238968Notes

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][CH:23]=[C:22]([O:26][C:27]([F:30])([F:29])[F:28])[CH:21]=3)(=[O:19])=[O:18])[CH:11]=2)[CH2:6]1)=O.Cl>C(O)C>[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][CH:23]=[C:22]([O:26][C:27]([F:30])([F:28])[F:29])[CH:21]=3)(=[O:19])=[O:18])[CH:13]=[CH:14][CH:15]=2)[CH2:6]1

Participants

Conditions

Temperature: 120 °C

Procedure

3-[3-(3-Trifluoromethoxy-benzenesulfonylamino)-phenyl]-pyrrolidine-1-carboxylic acid methyl ester (0.105 g; 0.24 mmol) were dissolved in 2.5 ml ethanol and 0.9 ml of concentrated HCl were added. The reaction mixture was heated in a microwave system (CEM) at 90-150° C. for several hours until consumption of starting material. The mixture was then concentrated in vacuo and the acidic aqueous phase extracted twice with diethylether. The aqueous phase was adjusted to pH 9 with 1 N aqueous NaOH, extracted three times with diethylether, and the combined organic layers dried over sodium sulfate, filtered and the solvent evaporated to dryness to yield 45 mg of the product.

Workup

concentrationThe mixture was then concentrated in vacuo
extractionthe acidic aqueous phase extracted twice with diethylether
extractionextracted three times with diethylether
dry with materialthe combined organic layers dried over sodium sulfate
filtrationfiltered
customthe solvent evaporated to dryness

Sources & evidence

ORD record: ord-bf39860572d5441ab6a39daa997349a0
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642642B2

Reaction notes

Loading…