Water → N-(2-Chloroethyl)-N'-beta-D-glucopyranosyl-N-nitrosourea

HRID 2083778

Reaktionsgleichung

Reaktionsgleichung von HRID 2083778
[Cl:1][CH2:2][CH2:3][NH:4][C:5]([NH:7][C@@H:8]1[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]([OH:12])[C@H:9]1[OH:10])=[O:6].[N:19]([O-])=[O:20].[Na+].O>C(O)=O>[Cl:1][CH2:2][CH2:3][N:4]([N:19]=[O:20])[C:5]([NH:7][C@@H:8]1[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]([OH:12])[C@H:9]1[OH:10])=[O:6]

Komponenten

5

Edukt 3

HCID 962WaterHCID 155713601-(2-chloroethyl)-3-(beta-D-glucopyranosyl)ureaHCID 23668193Sodium Nitrite

Produkt 1

HCID 9972891N-(2-Chloroethyl)-N'-beta-D-glucopyranosyl-N-nitrosoureaAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

A solution of 0.60 g of 1-(2-chloroethyl)-3-(β-D-glucopyranosyl)urea in 15 ml of 99% formic acid was admixed with 282 mg of sodium nitrite under ice-cooling and stirring. The mixture was stirred for 1 hour under ice-cooling to effect the nitrosation. The reaction mixture, after addition of 15 ml of cold water thereto, was ice-cooled for 30 minutes and then treated with 5 ml of Amberlite IR-120 (H+ form) for the removal of sodium cation. The reaction mixture so treated was concentrated to dryness below 30° C by distilling off the solvent under a reduced pressure. The residue was taken up into a small volume of n-propanol and the solution was admixed with a volume of petroleum ether to give precipitate. The precipitate which deposited was collected by filtration and then dried in a desiccator under vacuum, affording 0.65 g of the titled compound as an amorphous solid of pale yellow color. Yield 92%. mp. 85° C (decomposition). [α]D6 -14° (c 0.5, methanol).

Aufarbeitung

  1. temperaturecooling
  2. stirringThe mixture was stirred for 1 hour under ice-
  3. temperaturecooling
  4. temperaturecooled for 30 minutes
  5. additionThe reaction mixture so treated
  6. concentrationwas concentrated to dryness below 30° C
  7. distillationby distilling off the solvent under a reduced pressure
  8. customto give precipitate
  9. filtrationThe precipitate which deposited was collected by filtration
  10. customdried in a desiccator under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2b7d926b17e1424d94ab8f606d8f1622
Quelldatensatz
uspto-grants-1978_04
Patentnummer
US04086415

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