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

HRID 1777071Notes

Reaction equation

HRID 1777071 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 the morpholine (99 mg, 1.133 mmol) in presence of Potassiumcarbonate (313 mg, 2.266 mmol) in THF (Volume: 5 ml) at room temperature and reaction mixture allowed to stirred for 12 h at room temperature. Reaction was monitored by TLC. After completion of the reaction, Solvent was removed by vacuum and then compound was purified by column chromatography (3% CH3OH/CH2Cl2) afforded 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

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  5. customcompound was purified by column chromatography (3% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-247a24785875427eb37d10b01aef0f31
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

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