Hydrochloric Acid → HCID 66676232, compound

HRID 400530Notes

Reaction equation

HRID 400530 reaction equation
[CH:1]([N:4]([C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=1)[C:21]([O:23]CC)=[O:22])[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].[OH-].[K+].Cl>C(O)C>[CH:1]([N:4]([C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=1)[C:21]([OH:23])=[O:22])[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:9]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66676023HCID 66676023, compound

Product 1

HCID 66676232HCID 66676232, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethyl 3-(N-isopropyl-3-(tri fluoromethyl)phenylsulfonamido)benzoate (330 mg, 0.794 mmol) in ethanol (5 mL) was added 2 N KOH solution (2.4 mL). The mixture was stirred at room temperature for 3 days, and then 4 N HCl solution (1.3 mL) was added. The mixture was concentrated until the water was gone. Then dichloromethane/methanol (50:1, 50 mL) was added, the solution was filtered, and the filtrate was concentrated to give 3-(N-isopropyl-3-(trifluoromethyl)phenylsulfonamido)benzoic acid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.00 (d, 6H, J=8 Hz), 4.62 (m, 1H), 7.30 (m, 1H), 7.45 (s, 1H), 7.60 (m, 1H), 7.80-8.10 (m, 5H), 13.18 (br s, 1H); MS (ESI) m/z 416 (M−H)−.

Workup

  1. concentrationThe mixture was concentrated until the water
  2. additionThen dichloromethane/methanol (50:1, 50 mL) was added
  3. filtrationthe solution was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7b0c2ed4695844bda75ec648457523f4
Source dataset
uspto-grants-2014_06
Patent number
US08741899B2

Reaction notes

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