Methanol → HCID 1216839, compound

HRID 877633Notes

Reaction equation

HRID 877633 reaction equation
[N:1]1([S:6]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([OH:14])=[O:13])(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)(O)O.[CH3:23]O>>[N:1]1([S:6]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([O:14][CH3:23])=[O:13])(=[O:7])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 7676903-(Pyrrolidine-1-sulfonyl)benzoic acid

Product 1

HCID 1216839HCID 1216839, compoundYield 68.3%

Procedure

3-(pyrrolidin-1-ylsulfonyl)benzoic acid (200 mg, 0.783 mmol) was refluxed in the presence of con. Sulfuric acid (5.06 mg, 0.039 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 3-(pyrrolidin-1-ylsulfonyl)benzoate (150 mg, 0.535 mmol, 68.3% yield). 1H NMR (CDCl3, 400 MHz): δ 8.47 (m, 1H), 8.25 (d, 1H, J=7.6 Hz), 8.02 (dt, 1H, J=1.2 & 8.0 Hz), 7.63 (t, 1H, J=7.6 Hz), 3.96 (s, 3H), 3.27 (m, 4H), 1.77 (m, 4H). Mass [M+H]+: 270.1

Workup

  1. customReaction
  2. customAfter completion of the reaction, solvent
  3. customwas removed by vacuum
  4. customcompound was purified by flash chromatography

Sources & evidence

ORD record
ord-251ac76370644b22ac5c082807e6f40e
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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