Methanol → Methyl 4-(morpholin-4-ylsulfonyl)benzoate

HRID 877645Notes

Reaction equation

HRID 877645 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1.S(=O)(=O)(O)O.[CH3:24]O>>[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:24])=[O:15])=[CH:17][CH:18]=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 5594164-(Morpholine-4-sulfonyl)benzoic acid

Product 1

HCID 809900Methyl 4-(morpholin-4-ylsulfonyl)benzoateYield 84%

Procedure

4-(morpholinosulfonyl)benzoic acid (150 mg, 0.553 mmol) was refluxed in the presence of con. Sulfuric acid (3.57 mg, 0.028 mmol) in methanol at 70° C. for overnight. Reaction was monitored by TLC. After completion of the reaction, solvent was removed by vacuum and then compound was purified by flash chromatography afforded the methyl 4-(morpholinosulfonyl)benzoate (135 mg, 0.464 mmol, 84% yield). 1H NMR (CDCl3, 400 MHz): δ 8.21 (m, 2H), 7.82 (m, 2H), 3.97 (s, 3H), 3.4 (m, 4H), 3.02 (m, 4H). Mass [M+H]+:286.0

Workup

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Sources & evidence

ORD record
ord-910a0a0da5cf432696f2698ba4ee95d5
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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