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4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 2-{1-[2-(4-cyanophenoxy)ethyl]-3-methylureido}ethyl ester

HRID 899132
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 899132
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][CH2:8][CH2:9][N:10]([CH2:15][CH2:16][OH:17])[C:11]([NH:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)#[N:2].[Li]CCCC.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][N:10]([CH2:15][CH2:16][O:17][S:31]([C:28]2[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=2)(=[O:33])=[O:32])[C:11]([NH:13][CH3:14])=[O:12])=[CH:18][CH:19]=1)#[N:2]
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Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 690720791-[2-(4-Cyanophenoxy)ethyl]-1-(2-hydroxyethyl)-3-methylureaHCID 178418339Butyllithium

Produkt 1

HCID 86616243Toluene-4-sulfonic acid 2-{1-[2-(4-cyanophenoxy)ethyl]-3-methylureido}ethyl esterAusbeute 12,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

To a well-stirred solution of 1-[2-(4-cyanophenoxy)ethyl]-1-(2-hydroxy-ethyl)-3-methylurea (6.6 g, 0.0257 mol; see step (i) above) in dry THF (70 mL) was added n-BuLi (2.85 N, 1.766 g, 0.0276 mol) at −78° C., dropwise under a nitrogen atmosphere. After stirring at the same temperature for 45 min, p-toluenesulfonyl chloride (5.25 g, 0.0276 mol) in dry THF was added (drop by drop) and the reaction mixture was then stirred at −40° C. for 2 h. The reaction was quenched with 50 mL water and warmed to room temperature. The product was extracted with ethyl acetate, washed with brine solution and dried over sodium sulfate. Solvent evaporation under reduced pressure, followed by column chromatography over silica gel (using 15-25% methanol in chloroform) yielded 1.36 g of the title compound as a brown gummy liquid.

Aufarbeitung

  1. stirringthe reaction mixture was then stirred at −40° C. for 2 h
  2. customThe reaction was quenched with 50 mL water
  3. extractionThe product was extracted with ethyl acetate
  4. washwashed with brine solution
  5. dry with materialdried over sodium sulfate
  6. customSolvent evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d887d000e981418f99ffb3abff582464
Quelldatensatz
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07354917B2

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