Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-(Trifluoromethyl)aniline | HCID 9964 | — |
| Reactant | 2-Nitrobenzoyl chloride | HCID 11875 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 2123965 | HCID 2123965 | — |
Reaction Steps
A solution containing 2-nitrobenzoyl chloride (Fluka, Buchs, Switzerland) (1.97 mL, 15 mmol) and 4-dimethylaminopyridine (Fluka, Buchs, Switzerland) (10 mg) in dichloromethane (10 mL) is added to a stirred mixture of 4-aminobenzotrifluoride (Ruka, Buchs, Switzerland) (2.66 g, 16.5 mmol) and triethylamine (1.90 g, 18.8 mmol) in dichloromethane (100 mL) under an argon atmosphere and the mixture is stirred for 16 hours at 25° C. The stirred mixture is then treated with a saturated aqueous solution of sodium hydrogen carbonate (50 mL) and then extracted with dichoromethane (2×50 mL). The combined extracts are dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent 10-50% ethyl acetate in hexane, to give the title compound as a colourless crystalline solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06448277B2 |
|---|
| Source dataset | uspto-grants-2002_09 |
|---|
| ORD ID | ord-4cb134c8632e4cd291eba11f7546ebf2 |
|---|
| Source note | uspto-grants-2002_09 |
|---|