Morpholine → 3-(Morpholin-4-ylcarbonyl)benzenesulfonamide

HRID 331189

Reaction equation

HRID 331189 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=O)(=[O:4])=[O:3].C1N=CN(C(N2C=NC=C2)=O)C=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C1COCC1>[N:26]1([C:8]([C:7]2[CH:6]=[C:5]([S:2]([NH2:1])(=[O:3])=[O:4])[CH:13]=[CH:12][CH:11]=2)=[O:10])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 2293523-Sulfamoylbenzoic acid

Product 1

HCID 430898613-(Morpholin-4-ylcarbonyl)benzenesulfonamideYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(aminosulfonyl)benzoic acid (6 g, 0.029 mol) in THF (100 ml) at 0° C. is added CDI (5.8 g, 0.035 mol) and the mixture is stirred for 4 h. To this mixture morpholine (7.8 ml, 0.089 mol) is added dropwise and the mixture is stirred at room temperature for 15 h. The solvent is removed under vacuum and the residue is diluted with EtOAc (100 ml), washed with a 10% solution of sodium bicarbonate, water and brine. The solvent is removed under vacuum and the residue is taken up with small amount of water (15 ml) and stirred for 15 min. The solid is collected by filtration to afford 4 g (50%) of the title compound as a solid. 1H NMR (DMSO-d6, 400 MHz) δ 7.88-7.90 (1H, m), 7.83 (1H, s), 7.64-7.65 (2H, m), 7.47 (2H, bs), 3.56-3.64 (6H, m), 3.28-3.34 (2H, m); HPLC (Max plot) 98%, Rt, 4.09 min; LC/MS: (ES+): 206.2.

Workup

  1. stirringthe mixture is stirred at room temperature for 15 h
  2. customThe solvent is removed under vacuum
  3. additionthe residue is diluted with EtOAc (100 ml)
  4. washwashed with a 10% solution of sodium bicarbonate, water and brine
  5. customThe solvent is removed under vacuum
  6. stirringstirred for 15 min
  7. filtrationThe solid is collected by filtration

Sources & evidence

ORD record
ord-736eea8d938f40c7b629adf564e45d71
Source dataset
uspto-grants-2014_11
Patent number
US08877757B2

Linked notes

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