Furosemide → HCID 86613435, compound

HRID 2357744Notes

Reaction equation

HRID 2357744 reaction equation
[CH:1]1[CH:2]=[C:3]([CH2:6][NH:7][C:8]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]([S:17]([NH2:20])(=[O:19])=[O:18])=[C:10]([Cl:21])[CH:9]=2)[O:4][CH:5]=1.C(=O)(O)[O-].[Na+].[C:27](=[O:34])([S:31][CH2:32][CH3:33])[O:28][CH2:29]I>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.ClCCCl>[C:27](=[O:34])([S:31][CH2:32][CH3:33])[O:28][CH2:29][O:15][C:14](=[O:16])[C:13]1[CH:12]=[C:11]([S:17]([NH2:20])(=[O:19])=[O:18])[C:10]([Cl:21])=[CH:9][C:8]=1[NH:7][CH2:6][C:3]1[O:4][CH:5]=[CH:1][CH:2]=1

Participants

7

Reactant 3

HCID 3440Furosemide2×HCID 516892Sodium BicarbonateHCID 11436522(Ethylsulfanyl)(iodomethoxy)methanone

Product 1

HCID 86613435HCID 86613435, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

Furosemide (5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acid), (10) (Aldrich) (0.050 mole) is added to a stirred solution of sodium bicarbonate (0.100 mole) and tetrabutylammonium hydrogen sulfate (0.050 mole) in water (100 mL) at ambient temperature. After 10 minutes 1,2-dichloroethane (100 mL) is added and then after 30 minutes O-iodomethyl S-ethyl carbonothioate (0.050 mole) in 1,2-dichloroethane (25 mL) is added over 15 minutes. The mixture is stirred for 1 hour at ambient temperature. The organic layer is separated, washed with water (50 mL), dried (magnesium sulfate), and the solvent is evaporated. The residue is stirred with diethyl ether (100 mL), insoluble material is filtered off and washed with diethyl ether. The combined ether phases is evaporated, and the residue may be crystallized to give O-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxymethyl) S-ethyl carbonothioate (1005). See eg., Folkmann, et al., Synthesis, 1159 (1990), Method D.

Workup

  1. customThe organic layer is separated
  2. washwashed with water (50 mL)
  3. dry with materialdried (magnesium sulfate)
  4. customthe solvent is evaporated
  5. stirringThe residue is stirred with diethyl ether (100 mL), insoluble material
  6. filtrationis filtered off
  7. washwashed with diethyl ether
  8. customThe combined ether phases is evaporated
  9. customthe residue may be crystallized

Sources & evidence

ORD record
ord-e1f40676cc2748e7b4adbe9ccdc7c9aa
Source dataset
uspto-grants-2010_07
Patent number
US07763612B2

Reaction notes

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