Furosemide → 5-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyl chloride

HRID 2357747Notes

Reaction equation

HRID 2357747 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH:7]1[CH:8]=[C:9]([CH2:12][NH:13][C:14]2C(C(O)=O)=[CH:18][C:17]([S:23]([NH2:26])(=[O:25])=[O:24])=[C:16]([Cl:27])[CH:15]=2)[O:10][CH:11]=1>ClCCl>[NH2:26][S:23]([C:17]1[C:16]([Cl:27])=[CH:15][C:14]([NH:13][CH2:12][C:9]2[O:10][CH:11]=[CH:7][CH:8]=2)=[C:1]([CH:18]=1)[C:2]([Cl:4])=[O:3])(=[O:24])=[O:25]

Participants

4

Reactant 2

HCID 3440Furosemide2×HCID 65578Oxalyl chloride

Product 1

HCID 866134325-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of oxalyl chloride (0.040 mole) in dichloromethane (20 mL) is added dropwise to an ice bath cooled solution of furosemide (5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acid), (10) (Aldrich) (0.040 mole) in dichloromethane (50 mL). The reaction is stirred at ambient temperature for 5 hours. The reaction solution is washed with 5% aqueous sodium bicarbonate, with water, and then with a saturated sodium chloride solution. The organic layer is dried over sodium sulfate, filtered and concentrated in vacuo to give 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyl chloride (13). See D. L. Musso, et. al., J. Med. Chem., (2003) 46: 409.

Workup

  1. washThe reaction solution is washed with 5% aqueous sodium bicarbonate, with water
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7097387c96694381a567243c492ee92a
Source dataset
uspto-grants-2010_07
Patent number
US07763612B2

Reaction notes

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