Hydrochloric Acid → HCID 21075020, compound

HRID 1455336Notes

Reaction equation

HRID 1455336 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:7]=1[C:8]([O:10]C)=[O:9])(=[O:4])=[O:3].[OH-].[Li+].Cl>C1COCC1.O>[CH3:1][S:2]([NH:5][C:6]1[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][C:7]=1[C:8]([OH:10])=[O:9])(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21075150HCID 21075150, compound

Product 1

HCID 21075020HCID 21075020, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Preparation B5, Step 4: To a mixture of methyl 2-(methylsulfonamido)-5-(trifluoromethyl)benzoate (1.0 g, 3.367 mmol) in THF (20 ml) and water (20 ml) was added lithium hydroxide (0.4242 g, 10.10 mmol) and stirred at RT for 6 h. The reaction mixture was acidified with 1.5 N HCl and extracted with ethyl acetate (3×50 ml). The organic layer was washed with water, brine, dried (Na2SO4) and concentrated. The solid was filtered and dried under vaccum to get 2-(methylsulfonamido)-5-(trifluoromethyl)benzoic acid (0.7 g, 73%) as white solid. 1H NMR (400 MHz, CDCl3) δ 3.31 (s, 3H), 7.78 (d, 1H), 7.97 (d, 1H), 8.24 (s, 1H), 11.13 (bs, 1H); 13C NMR (100 MHz, CDCl3) δ 40.74, 116.5, 118.3, 122.8 (m), 128.8, 131.6, 144.3, 169.1. MS found: (M−H)−=282.

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. filtrationThe solid was filtered
  6. customdried under vaccum

Sources & evidence

ORD record
ord-68e5d69d98c74f3a90c150c4b2ab3aba
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

Loading…