Furosemide → 2,2,2-Trichloroethyl 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoate

HRID 2357749Notes

Reaction equation

HRID 2357749 reaction equation
[Cl:1][C:2]([Cl:6])([Cl:5])[CH2:3][OH:4].[NH2:7][S:8]([C:11]1[C:12]([Cl:27])=[CH:13][C:14]([NH:20][CH2:21][C:22]2[O:23][CH:24]=[CH:25][CH:26]=2)=[C:15]([CH:19]=1)[C:16](O)=[O:17])(=[O:10])=[O:9].C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C1C=CC=CC=1.C1(C)C=CC=CC=1>[NH2:7][S:8]([C:11]1[C:12]([Cl:27])=[CH:13][C:14]([NH:20][CH2:21][C:22]2[O:23][CH:24]=[CH:25][CH:26]=2)=[C:15]([CH:19]=1)[C:16]([O:4][CH2:3][C:2]([Cl:6])([Cl:5])[Cl:1])=[O:17])(=[O:9])=[O:10]

Participants

7

Reactant 3

HCID 3440FurosemideHCID 6101p-Toluenesulfonic acidHCID 8259Trichloroethanol

Product 1

HCID 593891212,2,2-Trichloroethyl 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent3×HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Benzene (30 mL) (or toluene) and 2,2,2-trichloroethanol (0.024 mole) are added to a round-bottomed flask. Furosemide (10) (5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acid, Aldrich) (0.025 mole), benzene (30 mL), and p-toluenesulfonic acid (0.001 mole) catalyst are added to the flask. A Dean-Stark trap is filled with benzene, and the contents of the flask are refluxed with stirring for several hours or until no additional water is collected in the trap. The reaction is cooled, extracted with sodium bicarbonate solution, washed with water, and then with a saturated sodium chloride solution. The organic layer may be dried over sodium sulfate, filtered and concentrated in vacuo to give 2,2,2-trichloroethyl 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoate. See Sandler et al., Organic Functional Group Preparations, (1968) p. 249.

Workup

  1. temperaturethe contents of the flask are refluxed
  2. customis collected in the trap
  3. temperatureThe reaction is cooled
  4. extractionextracted with sodium bicarbonate solution
  5. washwashed with water
  6. dry with materialThe organic layer may be dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86c1c11e39e742f2afd3f829221aac7b
Source dataset
uspto-grants-2010_07
Patent number
US07763612B2

Reaction notes

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