Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Nitric Acid | HCID 944 | — |
| Reactant | Cyanamide | HCID 9864 | — |
| Reactant | 3-Aminobenzonitrile | HCID 16702 | — |
| Reactant | HCID 178509849 | HCID 178509849 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 10308522 | HCID 10308522 | 46% |
Reaction Steps
N-(3-Cyanophenyl)guanidine.HNO3. To a solution of 3-aminobenzonitrile (3.31 g, 28 mmol) in EtOH (28 mL) was added cyanamide (2.5 mL of a 50% w/w solution in water). HNO3 (1.98 mL, 14.2 M) is added dropwise. The mixture was heated at an oil bath temperature of 100° C. for about 3 hours. The flask was allowed to cool to RT. Et2O (20 mL) was added and the solids isolated by filtration. The solids were dried under vacuum (1 torr) for about 18 hours to give the title compound as a beige powder (2.9 g, 46%). 1H-NMR (300 MHz, d6-DMSO) δ 9.80 (s, 1H), 7.77 (m, 2H), 7.69-7.57 (m, 6H); MS (ESI) (M+H)+ 161.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07582630B2 |
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| Source dataset | uspto-grants-2009_09 |
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| ORD ID | ord-b8ae895f9ca44d72a2ae8bbd5b1c3c2d |
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| Source note | uspto-grants-2009_09 |
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