Water → 2-[5-Chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carbonyl]benzoic acid

HRID 1898117Notes

Reaction equation

HRID 1898117 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:19]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([C:33]([F:36])([F:35])[F:34])[CH:27]=2)(=[O:25])=[O:24])COC)[C:5]([C:8]([C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=[O:13])=[O:9])=[N:6][CH:7]=1.O>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][S:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([C:33]([F:36])([F:35])[F:34])[CH:27]=2)(=[O:24])=[O:25])[C:5]([C:8]([C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=[O:13])=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 579423682-{5-Chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carbonyl}-benzoic acid

Product 1

HCID 116565312-[5-Chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carbonyl]benzoic acidYield 42.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-{5-Chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carbonyl}-benzoic acid (150 mg, 0.27 mmol) in 3 ml of 4M HCl in dioxane and 1 mL of water was refluxed for 2 hours. After cooling to room temperature the mixture was concentrated and then diluted with water. 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 (70% ethyl acetate in hexane) to afford 60 mg of title compound as an off white solid. MS: (M+H)/z=519.4.

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 (70% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-45b60cb85a3548f1b55e0cd4340e21cf
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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