Hydrochloric Acid → Venom
Reaction equation
[Cl-].[Na+].[CH3:3][NH:4][C:5](=[N:8][N+:9]([O-:11])=[O:10])OC.[OH-].[Na+].[O:14]1[CH2:18][CH2:17][CH:16]([CH2:19][NH2:20])[CH2:15]1.Cl>O.C(#N)C>[CH3:3][NH:4][C:5]([NH:20][CH2:19][CH:16]1[CH2:17][CH2:18][O:14][CH2:15]1)=[N:8][N+:9]([O-:11])=[O:10]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
14.0 g of sodium chloride and 53.8 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, and 4.3 g (0.05 mole) of 48% NaOH was further added to the suspension and stirred. Thereafter, [(3-tetrahydrofuryl)methyl]amine (38.0 g, 0.38 mole) was introduced dropwise to the suspension. 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 20 degree centigrade, and further stirred for 6 hours. Then, 35% hydrochloric acid (8.5 g, 0.08 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 96%.
Workup
- temperaturethe resulting mixture was cooled to −10 degree centigrade
- additionwas further added to the suspension
- stirringThe suspension was stirred at −10 degree centigrade for 4 hours
- temperatureheated to 20 degree centigrade
- stirringfurther stirred for 6 hours
Sources & evidence
- ORD record
- ord-62528e7bc5d44b29b3587b32de7ca0b2
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977496B2
Reaction notes
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