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Ethylenediamine → N-(2-Aminoethyl)isoquinoline-5-sulfonamide

HRID 247575
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 247575
[NH2:1][CH2:2][CH2:3][NH2:4].[CH:5]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([S:15](Cl)(=[O:17])=[O:16])[C:9]=2[CH:8]=[CH:7][N:6]=1.CO.C(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[NH2:1][CH2:2][CH2:3][NH:4][S:15]([C:10]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:14]=2[CH:13]=[CH:12][CH:11]=1)(=[O:16])=[O:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 3301EthylenediamineHCID 33716555-Isoquinolinesulfonyl chlorideHCID 21584188Chloroform methanol

Produkt 1

HCID 3544N-(2-Aminoethyl)isoquinoline-5-sulfonamideAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel3×

Versuchsvorschrift

In 200 ml of chloroform was dissolved 12.0 g of 1,2-diaminoethane, and to the solution was added dropwise 100 ml of a chloroform solution containing 4.55 g of 5-isoquinolinesulfonyl chloride under cooling with ice. After the dropwise addition of the chloroform solution, the mixed solution was stirred at a temperature of 20° C. to 25° C. for two hours, and then the reaction solution was extracted with a 10% aqueous hydrochloric acid solution. The pH of the aqueous layer was adjusted to 10 with a 10% aqueous sodium hydroxide solution, and the aqueous layer was extracted with chloroform. The chloroform layer extracted was washed with water and dried with anhydrous potassium carbonate. Then the chloroform was distilled from the chloroform layer, and the residue obtained was subjected to a column chromatography [silica gel: 200 g; developing solvent: 2% methanol/chloroform (volume ratio)] to give 3.3 g of N-(2-aminoethyl)-5-isoquinolinesulfonamide as an oily substace in a yield of 66%.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. extractionthe reaction solution was extracted with a 10% aqueous hydrochloric acid solution
  3. extractionthe aqueous layer was extracted with chloroform
  4. extractionThe chloroform layer extracted
  5. washwas washed with water
  6. dry with materialdried with anhydrous potassium carbonate
  7. distillationThen the chloroform was distilled from the chloroform layer
  8. customthe residue obtained

Quellen und Nachweise

ORD-Eintrag
ord-845614edcf494f7ba5f129e53db8d5d2
Quelldatensatz
uspto-grants-1987_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04709032

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