Hydrochloric Acid → HCID 21075115, compound

HRID 1171466Notes

Reaction equation

HRID 1171466 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[CH:5][C:6]([NH:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])=[C:7]([CH:12]=1)[C:8]([O:10]C)=[O:9].[OH-].[Li+].Cl>C1COCC1.O>[F:22][C:2]([F:1])([F:21])[C:3]1[CH:4]=[CH:5][C:6]([NH:13][S:14]([C:17]([F:18])([F:19])[F:20])(=[O:16])=[O:15])=[C:7]([CH:12]=1)[C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21075157HCID 21075157, compound

Product 1

HCID 21075115HCID 21075115, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-(trifluoromethyl)-2-(trifluoromethylsulfonamido)benzoate (2.7 g, 7.7 mmol) in 55 ml of THF was added lithium hydroxide (0.97 g, 23.1 mmol) in 55 ml of water and stirred at RT over night. The reaction mixture was acidified with 1.5N HCl and extracted with ethyl acetate. The organic layer was washed with water, brine and concentrated to give 5-(trifluoromethyl)-2-(trifluoromethylsulfonamido)benzoic acid (2 g) as white solid. 1H NMR (DMSO-d6, 400 MHz) δ 7.77 (m, 2H), 8.18 (s, 1H). MS found: (M−H)−=336.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d4b7fa5e4ab344758f610df9cc16c3f0
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

Loading…