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2-(Ethylamino)ethanol → N-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-phenyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide

HRID 1841598
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1841598
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:27])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[CH:9][CH:8]=1.[CH2:28]([NH:30][CH2:31][CH2:32][OH:33])[CH3:29]>CC(N(C)C)=O>[CH2:28]([N:30]([CH2:31][CH2:32][OH:33])[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:27])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[CH:9][CH:8]=1)[CH3:29]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 80722-(Ethylamino)ethanol2×HCID 23446540N-[4-(4-Bromo-butoxy)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide

Produkt 1

HCID 10183939N-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-phenyl)-N-methyl-4-trifluoromethyl-benzenesulfonamideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A solution of 466 mg (1 mmol) of N-[4-(4-Bromo-butoxy)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide 69-9844 in 3.5 ml DMA was treated at 0° C. with 0.195 ml (2 mmol) of 2-ethylaminoethanol and stirred at RT for 15 h. The reaction mixture was cooled (0° C.) again, treated with 0.195 ml (2 mmol) of 2-ethylaminoethanol and stirred at RT for further 24 h. The solution was concentrated, the residual oil was dissolved in water/acetontrile 1:1/5% formic acid and purified by prep. HPLC: RP-18, acetonitrile/water, 10%-60% acetonitrile. The pure fractions were collected, dissolved in EtOAc, washed with aqueous sat. NaHCO3 solution, and the organic phase was dried (Na2SO4) and evaporated to yield 360 mg (76%) of N-(4-{4-[Ethyl-(2-hydroxy-ethyl)-amino]-butoxy}-phenyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide, MS: 475 (MH+).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled (0° C.) again
  2. stirringstirred at RT for further 24 h
  3. concentrationThe solution was concentrated
  4. dissolutionthe residual oil was dissolved in water/
  5. custom1/5% formic acid and purified by prep
  6. customThe pure fractions were collected
  7. dissolutiondissolved in EtOAc
  8. washwashed with aqueous sat. NaHCO3 solution
  9. dry with materialthe organic phase was dried (Na2SO4)
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-44cb6206f3824baebb14b747c33bbfb0
Quelldatensatz
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06683201B2

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