HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → Benzamide, 2-fluoro-N-methoxy-N-methyl-3-(trifluoromethyl)-
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | 2-Fluoro-3-(trifluoromethyl)benzoic acid | HCID 518002 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Benzamide, 2-fluoro-N-methoxy-N-methyl-3-(trifluoromethyl)- | HCID 11196047 | 81.5% |
Reaction Steps
Ten grams (10 g 65 mmol) of 2-fluoro-3-(trifluoromethyl)benzoic acid and oxalyl chloride in 10 mL of anhydrous CH2Cl2 were treated with a few drops of DMF, and stirred at ambient temperature for 1 hour (gas evolution ceased). N,O-Dimethyhydroxylamine hydrochloride (16.8 g, 174 mmol) was added followed by 16 ml of pyridine. The reaction mixture was stirred overnight, then washed successively with H2O, 2 N HCl, and brine. The resulting solution was dried over sodium sulfate. Evaporation of solvents in vacuo gave 13.3 g of product as an oil, which was pure enough to be used in the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07592363B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-1e552925c9964dc999bcf070173862a5 |
| Source note | uspto-grants-2009_09 |