Morpholine → HCID 68853557, compound

HRID 1984041Notes

Reaction equation

HRID 1984041 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[NH:14][CH3:15])[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>C(OCC)(=O)C>[CH3:15][NH:14][C:13]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[S:2]([CH:18]1[O:19][CH2:20][CH2:21][NH:16][CH2:17]1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 57713890HCID 57713890, compound

Product 1

HCID 68853557HCID 68853557, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-(Chlorosulfonyl)-4-(methylamino)benzoic acid (1.2, 1.0 g) was dissolved in 20 mL of ethyl acetate and morpholine (Aa, 1.0 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-(methylamino)-3-(morpholino-sulfonyl)-benzoic acid (1.3.Aa) as an off-white powder (0.30 g, 30% yield). MS analysis (m−1)=299.

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-6d764d3af12242ccbf1626e48b87a39c
Source dataset
uspto-grants-2009_06
Patent number
US07544676B2

Reaction notes

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