Hydrochloric Acid → Venom

HRID 1012224Notes

Reaction equation

HRID 1012224 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][NH2:7])[CH2:2]1.[Cl-].[Na+].[OH-].[Na+].[CH3:12][NH:13][C:14](=[N:17][N+:18]([O-:20])=[O:19])OC.Cl>O.C(#N)C>[CH3:12][NH:13][C:14]([NH:7][CH2:6][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)=[N:17][N+:18]([O-:20])=[O:19]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium Chloride2×HCID 14798Sodium HydroxideHCID 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), 27.4 g of sodium chloride and 107.0 g of water were mixed, and the resulting mixture was cooled to −10 degree centigrade. Furthermore, 2.3 g (0.06 mole) of 96% NaOH was added to the solution and dissolved. Sodium chloride was dissolved in water with 78% of the saturated solubility at a water temperature of −10 degree centigrade. N,O-dimethyl-N′-nitroisourea (49.2 g, 0.37 mole) was introduced into the above solution, 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 95%.

Workup

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

Sources & evidence

ORD record
ord-9f06a58920ec461d9e81c4daf1ab2d08
Source dataset
uspto-grants-2011_07
Patent number
US07977496B2

Reaction notes

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