Hydrochloric Acid → Venom

HRID 1012226Notes

Reaction equation

HRID 1012226 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>[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

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium Chloride2×HCID 14798Sodium HydroxideHCID 10898660(Tetrahydrofuran-3-yl)methanamineHCID 136414659(E)-N-methyl-N'-nitromethoxymethanimidamide

Product 1

HCID 135779803VenomYield 81.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

[(3-tetrahydrofuryl)methyl]amine (43.3 g, 0.43 mole), 31.3 g of sodium chloride and 125 g of water were mixed, and the resulting mixture was cooled to −10 degree centigrade. Furthermore, 2.9 g (0.07 mole) of 96% NaOH was added to the solution and dissolved. Sodium chloride was dissolved in water with 76% 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 0 degree centigrade and further stirred for 18 hours. 35% hydrochloric acid (13.1 g, 0.13 mole) was added to the suspension so that the pH became not more than 4. The suspension was heated and dissolved for carrying out recrystallization. The precipitated crystal was filtered, and the filtered crystal was washed with cold water and then dried. 61 g of a 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine with a purity of 99% was obtained. The isolated yield at this time was 81%.

Workup

  1. temperaturethe resulting mixture was cooled to −10 degree centigrade
  2. dissolutiondissolved
  3. temperatureheated to 0 degree centigrade
  4. stirringfurther stirred for 18 hours
  5. temperatureThe suspension was heated
  6. dissolutiondissolved
  7. customrecrystallization
  8. filtrationThe precipitated crystal was filtered
  9. washthe filtered crystal was washed with cold water
  10. customdried

Sources & evidence

ORD record
ord-ed8cc61a55484679ab8dae3968d42445
Source dataset
uspto-grants-2011_07
Patent number
US07977496B2

Reaction notes

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