Hydrochloric Acid → Venom

HRID 1012228Notes

Reaction equation

HRID 1012228 reaction equation
[Cl-].[Na+].[OH-].[Na+].[O:5]1[CH2:9][CH2:8][CH:7]([CH2:10][NH2:11])[CH2:6]1.[CH3:12][NH:13][C:14](=[N:17][N+:18]([O-:20])=[O:19])OC.Cl>O>[CH3:12][NH:13][C:14]([NH:11][CH2:10][CH:7]1[CH2:8][CH2:9][O:5][CH2:6]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 78.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

18.75 g of sodium chloride, 115.0 g of water, 3.01 g (0.07 mole) of 96% NaOH and [(3-tetrahydrofuryl)methyl]amine (39.9 g, 0.39 mole) 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 53% of the saturated solubility at a water temperature of −10 degree centigrade. The solution was stirred at −10 degree centigrade for 4 hours, heated to 0 degree centigrade, and further stirred for 19 hours. Then, 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. 59 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 78%.

Workup

  1. temperaturethe resulting mixture was cooled to −10 degree centigrade
  2. temperatureheated to 0 degree centigrade
  3. stirringfurther stirred for 19 hours
  4. temperatureThe suspension was heated
  5. dissolutiondissolved
  6. customrecrystallization
  7. filtrationThe precipitated crystal was filtered
  8. washthe filtered crystal was washed with cold water
  9. customdried

Sources & evidence

ORD record
ord-bda7a982304a446e9e82ac2530fe68a3
Source dataset
uspto-grants-2011_07
Patent number
US07977496B2

Reaction notes

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