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

HRID 1438585Notes

Reaction equation

HRID 1438585 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:15]2[C:16]([C:22](=[O:31])[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:24]=3[Cl:30])=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)COC)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:32]([F:35])([F:34])[F:33].O>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:15]2[C:16]([C:22](=[O:31])[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:24]=3[Cl:30])=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)(=[O:9])=[O:10])=[CH:4][C:3]=1[C:32]([F:34])([F:35])[F:33]

Participants

5

Reactant 2

HCID 962WaterHCID 579422364-chloro-N-[5-chloro-2-(2-chloro-3-methyl-benzoyl)-pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

Product 1

HCID 579424274-chloro-N-[5-chloro-2-(2-chloro-3-methyl-benzoyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamideYield 64%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-chloro-N-[5-chloro-2-(2-chloro-3-methyl-benzoyl)-pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (58.6 mg, 1.03 mmol) in 4 N HCl in dioxane (4 mL) and water (1 mL) was stirred at 100° C. for overnight. The reaction mixture was cooled to room temperature, evaporated to dryness and treated with saturated aqueous NaHCO3 solution till pH 7-8. The mixture was extracted with EtOAc (2×25 mL), dried (anhydrous Na2SO4) and concentrated. The obtained residue was purified via column chromatography (SiO2, 70% EtOAc in hexanes) to afford 4-chloro-N-[5-chloro-2-(2-chloro-3-methyl-benzoyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide (34.5 mg) in 64% yield. 1H NMR (400 MHz, CDCl3) δ 11.00 (s, 1 H), 8.24 (d, 1 H), 8.18 (m, 1 H) 8.17 (d, 1 H), 7.98 (dd, 1 H), 7.63 (d, 1 H), 7.35 (d, 1 H), 7.24 (t, 1 H), 7.1 (d, 1 H), 2.37 (s, 3H); ESMS m/z (relative intensity): 522.9 (M+H)+ (100), 544.9 (M+Na)+ (100).

Workup

  1. customevaporated to dryness
  2. additiontreated with saturated aqueous NaHCO3 solution till pH 7-8
  3. extractionThe mixture was extracted with EtOAc (2×25 mL)
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated
  6. customThe obtained residue was purified via column chromatography (SiO2, 70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2403672c8d9f4497a646812a6808b185
Source dataset
uspto-grants-2009_11
Patent number
US07622583B2

Reaction notes

Loading…