Hydrochloric Acid → HCID 21075115, compound

HRID 2225151Notes

Reaction equation

HRID 2225151 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

Preparation B6, Step 4: 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-0a0383f140714e5f9e4c3e5add0aa1fb
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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