HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl iodide → 2-(4-dipropylaminomethyl-phenyl)-3-methyl-3H-benzimidazol-5-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | N-(2-amino-5-cyano-phenyl)-4-dipropylaminomethyl-benzamide | HCID 23155606 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-(4-dipropylaminomethyl-phenyl)-3-methyl-3H-benzimidazol-5-carbonitrile | HCID 23155390 | 26.4% |
Reaction Steps
The compound (613 mg) obtained in Example 29-4 was dissolved in THF (18 ml) and added with 60% sodium hydride (105 mg). After that, the whole was gradually added with methyl iodide (373 mg) and stirred at room temperature for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform, washed with water, and subjected to extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (160 mg) as a brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07932281B2 |
| Source dataset | uspto-grants-2011_04 |
| ORD ID | ord-d64a2e7e0dd5449daf462a96f37f5e7d |
| Source note | uspto-grants-2011_04 |