Methanol → Methyl 3-(morpholinosulfonyl)benzoate

HRID 1777014

Reaction equation

HRID 1777014 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([OH:15])=[O:14])(=[O:9])=[O:8])[CH2:3][CH2:2]1.OS(O)(=O)=O.[CH3:24]O>>[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([O:15][CH3:24])=[O:14])(=[O:9])=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2574763-(Morpholine-4-sulfonyl)benzoic acid

Product 1

HCID 779656Methyl 3-(morpholinosulfonyl)benzoate

Procedure

3-(Morpholinosulfonyl)benzoic acid (100 mg, 0.369 mmol) was refluxed overnight in methanol in the presence of catalytic concentrated H2SO4 at 65° C. 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 to yield the title compound as an off white solid (60 mg). 1H NMR (400 MHz, CDCl3): δ 8.38 (t, 1H, J=1.6 Hz), 8.27 (m, 1H), 7.92 (m, 1H), 7.64 (t, 1H, J=8.0 Hz), 3.95 (s, 3H), 3.73 (m, 4H), 3.00 (m, 4H). ESI-MS: 286.1 [M+H]+.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed by vacuum
  3. customcompound was purified by column chromatography

Sources & evidence

ORD record
ord-3e9c3a7dc800445ca5232c80f16a5d1c
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Linked notes

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