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Water → HCID 10930869, Verbindung

HRID 363397
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 363397
[C:1]1([CH3:50])[CH:6]=[CH:5][C:4]([S:7]([NH:10][CH2:11][CH2:12][N:13]([S:40]([C:43]2[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=2)(=[O:42])=[O:41])[CH2:14][CH2:15][N:16]([S:30]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[CH2:17][CH2:18][NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:54][CH2:55][O:56][CH2:57][CH2:58]Cl.O>CN(C=O)C>[C:26]1([CH3:29])[CH:27]=[CH:28][C:23]([S:20]([N:19]2[CH2:18][CH2:17][N:16]([S:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)(=[O:31])=[O:32])[CH2:15][CH2:14][N:13]([S:40]([C:43]3[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=3)(=[O:41])=[O:42])[CH2:12][CH2:11][N:10]([S:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:50])=[CH:2][CH:3]=3)(=[O:8])=[O:9])[CH2:58][CH2:57][O:56][CH2:55][CH2:54]2)(=[O:22])=[O:21])=[CH:24][CH:25]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8115Bis(2-chloroethyl) etherHCID 24758Sodium hydrideHCID 316681N,N'-ethane-1,2-diylbis[4-methyl-N-(2-{[(4-methylphenyl)sulfonyl]amino}ethyl)benzenesulfonamide]

Produkt 1

HCID 10930869HCID 10930869, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred solution of 1,4,7,10-tetra(p-toluenesulfonyl)-1,4,7,10-tetraazadecane prepared as in Example 15B (35.3 g, 0.0463 mole) in anhydrous DMF (460 ml) was added sodium hydride (2.77 g-80% in mineral oil, 0.0925 mole) in portions and the resulting mixture was stirred for 30 minutes under a dry argon atmosphere. The solution was then heated to 100° C. and a solution of 2-chloroethyl ether (6.61 g, 0.0463 mole) in anhydrous DMF (90 ml) was added dropwise over a 1.5 h period, maintaining the temperature at 100° C. After stirring the solution an additional 1.5 h at 100° C., H2O (3 l) was added while cooling (ice bath) to crystallize the product. The resulting tan solid was filtered and dried in vacuo. The crude product was purified by crystallization from CH2Cl2 -hexane to give 13.2 g (34% yield) of the product as an off-white solid: mp 197.5°-201° C.; 1H NMR (CDCl3) δ 2.44 (s, 12 H), 3.28 (m, 16 H), 3.57 (m, 4 H), 7.35 (m, 8 H), 7.69 (m, 8 H).

Aufarbeitung

  1. temperaturemaintaining the temperature at 100° C
  2. stirringAfter stirring the solution an additional 1.5 h at 100° C.
  3. temperaturewhile cooling (ice bath)
  4. customto crystallize the product
  5. filtrationThe resulting tan solid was filtered
  6. customdried in vacuo
  7. customThe crude product was purified by crystallization from CH2Cl2 -hexane

Quellen und Nachweise

ORD-Eintrag
ord-6e8d7753732648e386f1055faf76a112
Quelldatensatz
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05874421

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