Hydrochloric Acid → Venom

HRID 984061Notes

Reaction equation

HRID 984061 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

HCID 135779803VenomYield 53.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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: ethyl acetate/hexane=1/1) to obtain 7.8 g of 1-{(tetrahydro-3-furanyl)methyl}-2-nitro-3-methylguanidine (dinotefuran).

Workup

  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: ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-74b54c7dcc574c779fcb454415d761f5
Source dataset
uspto-grants-2005_03
Patent number
US06867223B2

Reaction notes

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