HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Chloride → [1-(2,6-Dichlorobenzyl)-4-nitro-1H-imidazol-2-yl]methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | Potassium sodium tartarate | HCID 9855836 | — |
| Reactant | Ethyl 1-(2,6-dichlorobenzyl)-4-nitro-1H-imidazole-2-carboxylate | HCID 67409298 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | [1-(2,6-Dichlorobenzyl)-4-nitro-1H-imidazol-2-yl]methanol | HCID 67410386 | — |
Reaction Steps
1200 mg (3.5 mmol) of the compound from Example 33A together with 15 mg (0.35 mmol) of lithium chloride were dissolved in 53 ml 1,2-dimethoxyethane, and 198 mg (5.23 mmol) of sodium borohydride were added at 0° C. The mixture was stirred at RT for 1 h. For work-up, 25 ml of a saturated potassium sodium tartrate solution were added with ice cooling and the mixture was extracted with 50 ml of ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:1). This gave 800 mg (76% of theory) of the target compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09187466B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-dd5f10d1e3d04799aab6c5d482bccdb3 |
| Source note | uspto-grants-2015_11 |