Sulfanilamide → 4-(2-(4-(3-Chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy)propanamido)benzenesulfonamide

HRID 1110674Notes

Reaction equation

HRID 1110674 reaction equation
Cl.[Cl:2][C:3]1[C:4]([O:13][C:14]2[CH:25]=[CH:24][C:17]([O:18][CH:19]([CH3:23])[C:20](Cl)=[O:21])=[CH:16][CH:15]=2)=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH2:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1.C(N(CC)CC)C>O1CCCC1>[Cl:2][C:3]1[C:4]([O:13][C:14]2[CH:25]=[CH:24][C:17]([O:18][CH:19]([CH3:23])[C:20]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([S:33]([NH2:36])(=[O:34])=[O:35])=[CH:29][CH:28]=3)=[O:21])=[CH:16][CH:15]=2)=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 5333SulfanilamideHCID 8471TriethylamineHCID 884514024-(3-Chloro-5-trifluoromethyl-2-pyridyloxy)phenoxypropionic acid chloride hydrochloride

Product 1

HCID 144985544-(2-(4-(3-Chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy)propanamido)benzenesulfonamideYield 80.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2-(4-(3-Chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy)propionic acid chloride hydrochloride (0.8 g) and 4-aminobenzene sulfonamide (0.5 g) were dissolved in dry tetrahydrofuran (20 ml), and the solution was stirred, with an addition of triethylamine (0.6 ml) at room temperature for 2 hours. After completion of the reaction, the solvent was evaporated under a reduced pressure, the residue was dissolved in methylene chloride and washed with 1N hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate, water and saturated aqueous sodium chloride. After drying over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under a reduced pressure was purified by medium pressure column chromatography by using silica gel, to obtain the title compound (0.8 g).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under a reduced pressure
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washwashed with 1N hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate, water and saturated aqueous sodium chloride
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe residue obtained by evaporation of the solvent under a reduced pressure
  7. customwas purified by medium pressure column chromatography

Sources & evidence

ORD record
ord-4dd32cb082864481a5ad96100b6af56c
Source dataset
uspto-grants-1990_12
Patent number
US04976773

Reaction notes

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