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

HRID 1711724Notes

Reaction equation

HRID 1711724 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 acid

Conditions

Temperature
110 °C

Procedure

A mixture of 4.26 2-chloro-5-methanesulfonyl-benzoic acid (Example A1(a)) and 91.8 mmol morpholine was heated at 110° C. for 15 h with shaking. The volatiles were removed in vacuo, and the residue was acidified with 4 M aq HCl and then further diluted with 150 ml 1 N aq HCl. The mixture was extracted three times with ethyl acetate, and the combined organic phases washed with brine and then dried over magnesium sulfate. Evaporation in vacuo yielded the title compound as a light-yellow amorphous solid. MS (m/e): 284.0 ([M−H]−1, 100%)

Workup

  1. customThe volatiles were removed in vacuo
  2. additionfurther diluted with 150 ml 1 N aq HCl
  3. extractionThe mixture was extracted three times with ethyl acetate
  4. washthe combined organic phases washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation in vacuo

Sources & evidence

ORD record
ord-c18f0aa2052d42f49b8553ab83dcf5e3
Source dataset
uspto-grants-2010_09
Patent number
US07790763B2

Reaction notes

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