Hydrochloric Acid → 3-(Morpholine-4-sulfonyl)-5-trifluoromethyl-benzoic acid

HRID 403382Notes

Reaction equation

HRID 403382 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([S:14]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)(=[O:16])=[O:15])[CH:5]=1.O.O.[OH-].[Li+].Cl>O1CCOCC1.C(OCC)(=O)C>[N:17]1([S:14]([C:6]2[CH:5]=[C:4]([CH:9]=[C:8]([C:10]([F:13])([F:11])[F:12])[CH:7]=2)[C:3]([OH:23])=[O:2])(=[O:15])=[O:16])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 70663402Methyl 3-(morpholinosulfonyl)-5-(trifluoromethyl)benzoate

Product 1

HCID 179642763-(Morpholine-4-sulfonyl)-5-trifluoromethyl-benzoic acidYield 100.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-(morpholine-4-sulfonyl)-5-trifluoromethyl-benzoic acid methyl ester (1.04 g, 2.94 mmol) in dioxane (10 mL) was added water (10 mL) and lithium hydroxide monohydrate (154 mg, 3.68 mmol) and the resulting clear solution was stirred at room temperature for 2 hours. The reaction mixture was poured on 1M aqueous hydrochloric acid (100 mL) and 100 mL ethyl acetate and the layers were separated. The aqueous layer was extracted a second time with ethyl acetate (100 mL). The organic layers were washed with brine (100 mL), dried over magnesium sulfate, filtered and concentrated under vacuum to give the desired compound as a colorless solid (1 g, 100%) which was pure for the next step without further purification. MS (ESI−): m/z=338.033 ([M−H]−).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted a second time with ethyl acetate (100 mL)
  3. washThe organic layers were washed with brine (100 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f00b25080f3a428c993b7c02d594a803
Source dataset
uspto-grants-2014_06
Patent number
US08748434B2

Reaction notes

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