Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | (Tetrahydrofuran-3-yl)methanamine | HCID 10898660 | — |
| Reactant | (E)-N-methyl-N'-nitromethoxymethanimidamide | HCID 136414659 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Venom | HCID 135779803 | — |
Reaction Steps
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%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07977496B2 |
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| Source dataset | uspto-grants-2011_07 |
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| ORD ID | ord-62528e7bc5d44b29b3587b32de7ca0b2 |
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| Source note | uspto-grants-2011_07 |
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