Hydrochloric Acid → Venom

HRID 1012223Notes

Reaction equation

HRID 1012223 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][NH2:7])[CH2:2]1.[Cl-].[Na+].[CH3:10][NH:11][C:12](=[N:15][N+:16]([O-:18])=[O:17])OC.Cl>O.C(#N)C>[CH3:10][NH:11][C:12]([NH:7][CH2:6][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)=[N:15][N+:16]([O-:18])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium Chloride2×HCID 10898660(Tetrahydrofuran-3-yl)methanamineHCID 136414659(E)-N-methyl-N'-nitromethoxymethanimidamide

Product 1

HCID 135779803Venom

Reagents, catalysts & solvents 2

HCID 962WaterSolvent4×HCID 6342AcetonitrileSolvent

Procedure

[(3-tetrahydrofuryl)methyl]amine (38.0 g, 0.38 mole), 31.3 g of sodium chloride and 125.0 g of water were mixed, and the resulting mixture was cooled to −10 degree centigrade. N,O-dimethyl-N′-nitroisourea (49.2 g, 0.37 mole) was introduced into the above solution. Sodium chloride was dissolved in water with 76% of the saturated solubility at a water temperature of −10 degree centigrade. The suspension was stirred at −10 degree centigrade for 4 hours and then heated to 10 degree centigrade, and further stirred for 19 hours. 35% hydrochloric acid (6.7 g, 0.07 mole) was added to the suspension so that the pH became not more than 4. Water and acetonitrile were added to the above suspension for complete dissolution. The resulting solution was analyzed by HPLC and as a result, the reaction yield of the titled compound was 88%.

Workup

  1. temperaturethe resulting mixture was cooled to −10 degree centigrade
  2. temperatureheated to 10 degree centigrade
  3. stirringfurther stirred for 19 hours

Sources & evidence

ORD record
ord-dd5c540172bd41bfb7a460c58dd82268
Source dataset
uspto-grants-2011_07
Patent number
US07977496B2

Reaction notes

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