Methanol → Methyl 4-fluoro-3-(morpholin-4-ylsulfonyl)benzoate

HRID 1777021Notes

Reaction equation

HRID 1777021 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:11]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)(=[O:13])=[O:12].S(=O)(=O)(O)O.[CH3:25]O>>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:25])=[O:7])=[CH:4][C:3]=1[S:11]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)(=[O:12])=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 6927164-Fluoro-3-(morpholine-4-sulfonyl)benzoic acid

Product 1

HCID 700043Methyl 4-fluoro-3-(morpholin-4-ylsulfonyl)benzoate

Procedure

4-Fluoro-3-(morpholinosulfonyl)benzoic acid (50 mg, 0.173 mmol) was refluxed overnight in the presence of concentrated sulfuric acid (1.117 mg, 8.64 μmol) in methanol (8 mL) at 70° C. The reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum and compound was purified by column chromatography affording the title compound (20 mg). 1H NMR (400 MHz, CD3OD): δ 8.42 (dd, 1H, J=2.0 & 6.4 Hz), 8.33 (m, 1H), 7.49 (t, 1H, J=8.8 Hz), 3.94 (s, 3H), 3.71 (m, 4H), 3.16 (m, 4H).

Workup

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

Sources & evidence

ORD record
ord-0bf541203d7f4a4bb9b7843e60db306b
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

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