Furosemide → HCID 59389122, compound

HRID 2357758Notes

Reaction equation

HRID 2357758 reaction equation
[NH2:1][S:2]([C:5]1[C:6]([Cl:21])=[CH:7][C:8]([NH:14][CH2:15][C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:4])=[O:3].O1CCOCC1.C(=O)([O-])[O-].[Cs+:32].[Cs+]>O>[NH2:1][S:2]([C:5]1[C:6]([Cl:21])=[CH:7][C:8]([NH:14][CH2:15][C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)=[C:9]([CH:13]=1)[C:10]([O-:12])=[O:11])(=[O:3])=[O:4].[Cs+:32]

Participants

5

Reactant 3

HCID 3440FurosemideHCID 10796Cesium carbonateHCID 312751,4-Dioxane

Product 1

HCID 59389122HCID 59389122, compoundYield 191.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Furosemide (10) (5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acid, Aldrich) (4.0 g, 12.1 mmol) was added to dioxane (100 mL), and water (50 mL) was added with stirring to give a solution. Cesium carbonate (1.97 g, 6.0 mmol) was added, and the clear solution was stirred for 1 hour. The solvent was removed by spin evaporation, and the solid was dried overnight on a vacuum pump to afford 5.31 g of cesium 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoate as a white solid.

Workup

  1. additionwas added
  2. customto give a solution
  3. stirringthe clear solution was stirred for 1 hour
  4. customThe solvent was removed by spin evaporation
  5. customthe solid was dried overnight on a vacuum pump

Sources & evidence

ORD record
ord-2f979fa50562443ab0857af1c1c8fbfa
Source dataset
uspto-grants-2010_07
Patent number
US07763612B2

Reaction notes

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