Hydrochloric Acid → Venom

HRID 1397182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1397182
[H-].[Na+].[CH3:3][N:4]1CN(C)[CH2:7][NH:6][C:5]1=[N:11][N+:12]([O-:14])=[O:13].O(C[CH:24]1[CH2:28][CH2:27][O:26][CH2:25]1)S(C(F)(F)F)(=O)=O.Cl.C(=O)(O)[O-].[Na+]>CN(C=O)C>[O:26]1[CH2:27][CH2:28][CH:24]([CH2:7][NH:6][C:5]([NH:4][CH3:3])=[N:11][N+:12]([O-:14])=[O:13])[CH2:25]1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 216645293-Tetrahydrofuranylmethyl triflateHCID 135476318N-(1,5-dimethyl-1,3,5-triazinan-2-ylidene)nitramide

Produkt 1

HCID 135779803VenomAusbeute 53,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture comprising 10.0 g of (tetrahydro-3-furanyl)methanol, 29.5 g of trifluoromethanesulfonic anhydride, 10.0 g of pyridine and 200 ml of dichloromethane was stirred for an hour at room temperature. Water was poured into the reaction solution to separate the organic layer, which was washed with 1 N hydrochloric acid, water and a saturated saline solution, dried, and concentrated to obtain 20 g of 3-tetrahydro-furanylmethyl triflate. 3.25 g of 60% sodium hydride were added to 12.5 g of 1,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine and 60 ml of DMF at room temperature, followed by stirring for an hour. 20.0 g of the 3-tetrahydrofuranylmethyl triflate were added thereto, and the mixture was stirred at 50° C. for 2 hours. After cooling the mixture to room temperature, 50 ml of 2N hydrochloric acid were added thereto, followed by stirring at 50° C. for 2 hours. The resultant mixture was neutralized with sodium bicarbonate and extracted with dichloromethane, and the extract was dried and concentrated. The residue thus obtained was purified by silica gel column chromatography (eluent: 1:1 ratio of ethyl acetate/hexane) to obtain 7.8 g of 1-{(tetrahydro-3-furanyl)methyl}-2-nitro-3-methylguanidine (dinotefuran).

Aufarbeitung

  1. stirringthe mixture was stirred at 50° C. for 2 hours
  2. stirringby stirring at 50° C. for 2 hours
  3. extractionextracted with dichloromethane
  4. customthe extract was dried
  5. concentrationconcentrated
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography (eluent: 1:1 ratio of ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-10c5fa4888ff4d7eb1f603e110357fca
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901154B2

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