Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 86616333 | HCID 86616333 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178474184 | HCID 178474184 | 28.9% |
Reaction Steps
To a solution of 1-(4-iodophenyl)pyridine-2(1H)-thione (384 mg, 1.23 mmol) in CH3CN (10 mL), CH3I (0.80 mL, 12.8 mmol) was added. After being stirred at room temperature overnight, the mixture was concentrated in vacuo to give a solid. The solid was dissolved in DMF (6 mL). To the solution, NH3 in MeOH (7N, 3.0 mL, 21.0 mmol) and triethylamine (1.5 mL, 10.8 mmol) were added. After being stirred at room temperature overnight, the mixture was purified by HPLC to give a solid. The solid was dissolved in pyridine (3 mL) and CH2Cl2 (3 mL). To the solution, acetyl chloride (0.200 mL, 2.8 mmol) was added. After being stirred at room temperature overnight, the mixture was purified by HPLC to give (E)-N-(1-(4-iodophenyl)pyridin-2(1H)-ylidene)acetamide (120 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08063077B2 |
|---|
| Source dataset | uspto-grants-2011_11 |
|---|
| ORD ID | ord-9b43f3ab1b4844c1a0b6cab4b79004bf |
|---|
| Source note | uspto-grants-2011_11 |
|---|