Morpholine → 3-(Morpholine-4-sulfonyl)benzoic acid

HRID 877598

Reaction equation

HRID 877598 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[O:17]1[CH2:18][CH2:19][N:14]([S:2]([C:5]2[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=2)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 77641Benzoic acid, 3-(chlorosulfonyl)-

Product 1

HCID 2574763-(Morpholine-4-sulfonyl)benzoic acidYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(Chlorosulfonyl)benzoic acid (250 mg, 1.133 mmol) was added to morpholine (99 mg, 1.133 mmol) in the presence of potassium carbonate (313 mg, 2.266 mmol) in THF (5 mL) at room temperature, and reaction mixture allowed to stirred for 12 h at rt. The reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum, and then compound was purified by column chromatography (3% CH3OH/CH2Cl2) affording the title compound (160 mg) as a solid. 1H NMR (400 MHz, CD3OD): δ 8.34 (m, 1H), 8.32 (d, 1H, J=8.0 Hz), 7.99 (m, 1H), 7.76 (t, 1H, J=8.0 Hz), 3.70 (m, 4H), 2.98 (m, 4H). ESI-MS: 272.0 [M+H]+.

Workup

  1. customreaction mixture
  2. customAfter completion of the reaction
  3. customthe solvent was removed by vacuum
  4. customcompound was purified by column chromatography (3% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-ecaec209cb1f4c859c0307cebaa5c84c
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Linked notes

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