Hydrochloric Acid → 3-{[4-(Trifluoromethyl)phenyl]sulfamoyl}benzoic acid

HRID 1951503Notes

Reaction equation

HRID 1951503 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=2)[C:16]([O:18]CC)=[O:17])(=[O:12])=[O:11])=[CH:5][CH:4]=1.C(O)C.[OH-].[Na+].Cl>O>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][S:10]([C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=2)[C:16]([OH:18])=[O:17])(=[O:11])=[O:12])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 66675205Ethyl 3-({[4-(trifluoromethyl)phenyl]amino}sulfonyl)benzoate

Product 1

HCID 253351443-{[4-(Trifluoromethyl)phenyl]sulfamoyl}benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the product of Step A was added ethanol (25 mL) followed by a solution of NaOH (1.93 g, 48.3 mmol) in water (25 mL). The reaction was stirred at ambient temperature for 1.5 hours. To the mixture was added dropwise 1 N HCl (95 mL), and the mixture was stirred at ambient temperature overnight. The solids were collected by filtration, washed with water (2×20 mL), and dried in a vacuum oven at 45° C. overnights to give 3-({[4-(trifluoromethyl)phenyl]amino}sulfonyl)benzoic acid: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.28 (d, J=8.4 Hz, 2H), 7.62 (d, J=8.5 Hz, 2H), 7.71 (t, J=7.8 Hz, 1H), 8.03 (ddd, J=7.8, 1.9, 1.1 Hz, 1H), 8.15 (dt, J=7.8, 1.4 Hz, 1H), 8.34 (t, J=1.7 Hz, 1H), 10.98 (s, 1H), 13.54 (s, 1H); MS (ESI) m/z 344 (M−H)−.

Workup

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. filtrationThe solids were collected by filtration
  3. washwashed with water (2×20 mL)
  4. customdried in a vacuum oven at 45° C. overnights

Sources & evidence

ORD record
ord-189a30b217374cd18bc5aa4be3c4a137
Source dataset
uspto-grants-2013_03
Patent number
US08404719B2

Reaction notes

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