Sodium Hydroxide → N-{5-[(5-Oxo-4,5-dihydro-1H-imidazol-2-ylamino)-methyl]-naphthalen-2-yl}-benzenesulfonamide

HRID 492094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 492094
[NH2:1][CH2:2][CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:6]=[CH:5][C:4]1=2.CS[C:25]1[NH:29][C:28](=[O:30])[CH2:27][N:26]=1.[OH-].[Na+]>C(O)C>[O:30]=[C:28]1[NH:29][C:25]([NH:1][CH2:2][C:3]2[CH:12]=[CH:11][CH:10]=[C:9]3[C:4]=2[CH:5]=[CH:6][C:7]([NH:13][S:14]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])=[CH:8]3)=[N:26][CH2:27]1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 137567813,5-dihydro-2-(methylthio)-4H-Imidazol-4-oneHCID 57678964N-(5-aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide

Produkt 1

HCID 68831349N-{5-[(5-Oxo-4,5-dihydro-1H-imidazol-2-ylamino)-methyl]-naphthalen-2-yl}-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of N-(5-Aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide, 2-methylsulfanyl-3,5-dihydro-imidazol-4-one (prepared by the method reported by Chen et al., WO9736859) and sodium hydroxide in ethanol is heated to reflux, then concentrated under reduced pressure, diluted with ethyl acetate, and washed with aqueous sodium carbonate. The organic phase is dried (magnesium sulfate) and concentrated under reduced pressure to give N-{5-[(5-Oxo-4,5-dihydro-1H-imidazol-2-ylamino)-methyl]-naphthalen-2-yl}-benzenesulfonamide. 5-[(5-Oxo-4,5-dihydro-1H-imidazol-2-ylamino)-methyl]-naphthalene-2-sulfonic acid phenylamide may be similarly prepared.

Aufarbeitung

  1. customprepared by the method
  2. temperatureis heated
  3. temperatureto reflux
  4. concentrationconcentrated under reduced pressure
  5. additiondiluted with ethyl acetate
  6. washwashed with aqueous sodium carbonate
  7. dry with materialThe organic phase is dried (magnesium sulfate)
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7d9232266f504c76a382b861a5fbb398
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531577B2

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