Hydrochloric Acid → N-Hydroxy-4-morpholin-4-yl-1,2,5-oxadiazole-3-carboximidoyl chloride

HRID 1663501Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1663501
[OH:1][N:2]=[C:3]([C:5]1[C:9]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:8][O:7][N:6]=1)N.N([O-])=O.[Na+].[ClH:20]>O>[OH:1][N:2]=[C:3]([Cl:20])[C:5]1[C:9]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:8][O:7][N:6]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 136335830N'-hydroxy-4-morpholin-4-yl-1,2,5-oxadiazole-3-carboximidamide

Produkt 1

HCID 136335829N-Hydroxy-4-morpholin-4-yl-1,2,5-oxadiazole-3-carboximidoyl chlorideAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of N′-hydroxy-4-morpholin-4-yl-1,2,5-oxadiazole-3-carboximidamide (66 mg, 0.3 mmol) in 6.0 M HCl (0.62 mL) at 5-10° C. was treated with a solution of sodium nitrite (32 mg, 0.47 mmol) in water (0.5 mL) dropwise and stirred for 2 h at 0° C. The suspension was filtered and the solid washed with ice water to give desired product (22 mg, 30%). The filtrate was extracted with ethyl acetate (30 mL) which was washed with brine (10 mL), filtered and concentrated to give additional product (23 mg, 32%) that contained minor impurities. The combined material was used immediately in the next step.

Aufarbeitung

  1. filtrationThe suspension was filtered
  2. washthe solid washed with ice water

Quellen und Nachweise

ORD-Eintrag
ord-e21d5a328546417ba9c03c5f13908a27
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08034953B2

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