HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phosgene → rac-(4S*,5R*)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phosgene | HCID 6371 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 67205372 | HCID 67205372 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | rac-(4S*,5R*)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride | HCID 76588499 | — |
Reaction Steps
To a solution of rac-5-[(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl]-2-tert-butyl-4-ethoxy-pyridine (20 mg) and triethylamine (200 uL, 1.43 mmol) in 5 mL of methylene chloride at 0° C. was added 0.3 mL of 1.9 M phosgene in toluene solution (Fluka). After stirring for 30 min the mixture was taken up in methylene chloride and washed with water, dried over anhydrous sodium sulfate, filtered and concentrated to give rac-(4S*,5R*)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride as a white solid (22 mg). It was used in the next reaction without purification
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08513239B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-ede6e9f358c049fa9f9bb1ead1c82f6c |
| Source note | uspto-grants-2013_08 |