Water → N-[2-(2-Bromo-benzoyl)-5-chloro-pyridin-3-yl]-4-chloro-3-trifluoromethyl-benzenesulfonamide

HRID 1898124Notes

Reaction equation

HRID 1898124 reaction equation
[Br:1][C:2]1[CH:34]=[CH:33][CH:32]=[CH:31][C:3]=1[C:4]([C:6]1[C:11]([N:12](COC)[S:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([C:23]([F:26])([F:25])[F:24])[CH:17]=2)(=[O:15])=[O:14])=[CH:10][C:9]([Cl:30])=[CH:8][N:7]=1)=[O:5].O>Cl.O1CCOCC1>[Br:1][C:2]1[CH:34]=[CH:33][CH:32]=[CH:31][C:3]=1[C:4]([C:6]1[C:11]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([C:23]([F:24])([F:26])[F:25])[CH:17]=2)(=[O:14])=[O:15])=[CH:10][C:9]([Cl:30])=[CH:8][N:7]=1)=[O:5]

Participants

5

Reactant 2

HCID 962WaterHCID 57942367HCID 57942367, compound

Product 1

HCID 11685431N-[2-(2-Bromo-benzoyl)-5-chloro-pyridin-3-yl]-4-chloro-3-trifluoromethyl-benzenesulfonamideYield 54%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-[2-(2-Bromo-benzoyl)-5-chloro-pyridin-3-yl]-4-chloro-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (100 mg, 0.167 mmol) in 3 ml of 4M HCl in dioxane and 1 mL of water was refluxed for 3 hours. After cooling to rt the mixture was concentrated, diluted with water and then sodium bicarbonate was added until pH was 6. The mixture was extracted with ethyl acetate, dried and concentrated. The residue was further purified via flash column (30% ethyl acetate in hexane) to afford 50 mg of title compound as an off white solid. MS: (M+H)/z=555.3, (M+Na)/z=575.3.

Workup

  1. concentrationwas concentrated
  2. additiondiluted with water
  3. additionsodium bicarbonate was added until pH was 6
  4. extractionThe mixture was extracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was further purified via flash column (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-74dd8e196bda4f56ad5f125c9d602f6f
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

Loading…