Morpholine → 5-(Methanesulfonyl)-2-(morpholin-4-yl)benzoic acid

HRID 225703Notes

Reaction equation

HRID 225703 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>>[CH3:14][S:11]([C:8]1[CH:9]=[CH:10][C:2]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])(=[O:13])=[O:12]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 23291322-Chloro-5-(methylsulphonyl)benzoic acid

Product 1

HCID 211003195-(Methanesulfonyl)-2-(morpholin-4-yl)benzoic acidYield 58%

Conditions

Temperature
110 °C

Procedure

A mixture of 4.26 mmol 2-chloro-5-methanesulfonyl-benzoic acid (Example B1(a)) in 8 ml morpholine was heated at 110° C. for 15 h. After evaporation of all volatiles the residue was acidified by addition of 1 N HCl and extracted three times with ethyl acetate. The combined organic extracts were washed sequentially with 1 N HCl and saturated brine, dried over sodium sulphate, and concentrated in vacuo to afford the title compound as a light yellow amorphous solid (58%). MS (m/e): 284.1 ([M−H]−, 100%).

Workup

  1. customAfter evaporation of all volatiles the residue
  2. additionwas acidified by addition of 1 N HCl
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic extracts were washed sequentially with 1 N HCl and saturated brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae9ab6bdff7145bb8302a1e6ee771747
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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