Hydrochloric Acid → N-ethyl-N'-(beta-D-xylosyl)-N-nitrosourea

HRID 542246

Reaktionsgleichung

Reaktionsgleichung von HRID 542246
O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].[CH2:11]([NH:13][C:14]([NH2:16])=[O:15])[CH3:12].[N+:17](NC1C=CC=CC=1)([O-])=[O:18].Cl>C(O)C.O>[CH2:11]([N:13]([N:17]=[O:18])[C:14]([NH:16][C@@H:9]1[O:10][CH2:2][C@@H:3]([OH:4])[C@H:5]([OH:6])[C@H:7]1[OH:8])=[O:15])[CH3:12]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 12254EthylureaHCID 61191N-NitroanilineHCID 644160aldehydo-D-Xylose

Produkt 1

HCID 86741402N-ethyl-N'-(beta-D-xylosyl)-N-nitrosourea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 3 g of D-xylose, 1.9 g of ethylurea, 0.3 g of nitroaniline and 0.2 ml of a concentrated hydrochloric acid is refluxed in 15 ml of ethanol for 10 minutes. The precipitate in the amount of 2.8 g is separated, then added with 15 ml of glacial acetic acid, 2.5 ml of distilled water and 1.74 g of sodium nitrite and stirred for 2 hours at 0° C. The solution is evaporated and recrystallized from an alcohol to give 2.54 g (80% of the theoretical) of the product. M.p. 104° C. (decomposition), [α]D -13.6° (water), Rf =0.76. Found, %: N 16,42. Calculated, %: N 16.86.

Aufarbeitung

  1. customThe precipitate in the amount of 2.8 g is separated
  2. additionadded with 15 ml of glacial acetic acid, 2.5 ml of distilled water and 1.74 g of sodium nitrite
  3. customThe solution is evaporated
  4. customrecrystallized from an alcohol
  5. customto give 2.54 g (80% of the theoretical) of the product

Quellen und Nachweise

ORD-Eintrag
ord-ce909d904dd84cc9a1a00a02549b3645
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04656259

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