Methanol → HCID 16413657, compound

HRID 877640Notes

Reaction equation

HRID 877640 reaction equation
[O:1]=[S:2]1(=[O:17])[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([OH:13])=[O:12])[CH2:4][CH2:3]1.S(=O)(=O)(O)O.[CH3:23]O>>[O:17]=[S:2]1(=[O:1])[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([O:13][CH3:23])=[O:12])[CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2764466HCID 2764466, compound

Product 1

HCID 16413657HCID 16413657, compoundYield 90%

Procedure

3-(1,1-dioxidothiomorpholino)benzoic acid (100 mg, 0.392 mmol) was refluxed in the presence of con. Sulfuric acid (2.53 mg, 0.020 mmol) in methanol (5 mL) at 70° C. for overnight. Reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum and then compound was purified by flash chromatography afforded the methyl 3-(1,1-dioxidothiomorpholino)benzoate (99 mg, 0.353 mmol, 90% yield). 1H NMR (CDCl3, 400 MHz): δ 7.58 (m, 2H), 7.36 (t, 1H, J=8.0 Hz), 7.09 (m, 1H), 3.91 (s, 3H), 3.89 (m, 4H), 3.11 (m, 4H). Mass [M+H]+: 270.1

Workup

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

Sources & evidence

ORD record
ord-77a0175eee45418f9c3a027c49faa1f2
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

Loading…