Hydrochloric Acid → Venom

HRID 1012222Notes

Reaction equation

HRID 1012222 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][NH2:7])[CH2:2]1.[OH-].[Na+].[CH3:10][NH:11][C:12](=[N:15][N+:16]([O-:18])=[O:17])OC.Cl>C(#N)C.O>[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 14798Sodium HydroxideHCID 10898660(Tetrahydrofuran-3-yl)methanamineHCID 136414659(E)-N-methyl-N'-nitromethoxymethanimidamide

Product 1

HCID 135779803Venom

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

[(3-tetrahydrofuryl)methyl]amine (38.0 g, 0.38 mole) and 56.99 g of water were mixed, and the resulting mixture was cooled to 5 degree centigrade. Furthermore, 3.05 g (0.07 mole) of 1N NaOH was added to the solution, and then N,O-dimethyl-N′-nitroisourea (49.2 g, 0.37 mole) was introduced to the solution. The suspension was stirred at 5 degree centigrade for 4 hours, and then heated to 10 degree centigrade, and further stirred for 10 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 86%.

Workup

  1. temperaturethe resulting mixture was cooled to 5 degree centigrade
  2. temperatureheated to 10 degree centigrade
  3. stirringfurther stirred for 10 hours

Sources & evidence

ORD record
ord-d15e72138a2c471f9b32dd80a15f31da
Source dataset
uspto-grants-2011_07
Patent number
US07977496B2

Reaction notes

Loading…