Morpholine → 4-Bromo-3-(morpholine-4-sulfonyl)benzoic acid

HRID 1984048Notes

Reaction equation

HRID 1984048 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:11](Cl)(=[O:13])=[O:12].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:11]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 37373734-Bromo-3-(chlorosulfonyl)benzoic acid

Product 1

HCID 7679034-Bromo-3-(morpholine-4-sulfonyl)benzoic acidYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Bromo-3-chlorosulfonyl-benzoic acid (2.2, 1.1 g) was dissolved in 20 mL of ethyl acetate and morpholine (Aa, 1.48 mL, 3 eq) was added. The mixture was stirred at room temperature for 2 hours, then extracted with 15 mL of 0.5M HCl. The organic layer was washed with H2O and brine and the solvent evaporated to yield 4-bromo-3-(morpholinosulfonyl)-benzoic acid (2.3.Aa) as an off-white powder (1.13 mg, 88% yield). MS analysis (m−1)=348.

Workup

  1. extractionextracted with 15 mL of 0.5M HCl
  2. washThe organic layer was washed with H2O and brine
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-8a003b9b30ce4c63903cca75f367e09d
Source dataset
uspto-grants-2009_06
Patent number
US07544676B2

Reaction notes

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