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

HRID 655616Notes

Reaction equation

HRID 655616 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 polt) 98%, Rt, 4.09 min; LCMS: (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-906d9e771c424c2a856f129a3cf88c5c
Source dataset
uspto-grants-2011_12
Patent number
US08071597B2

Reaction notes

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