HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 4-chloro-2-fluoro-N-methoxy-N-methylbenzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | 4-Chloro-2-fluorobenzoic acid | HCID 99152 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-chloro-2-fluoro-N-methoxy-N-methylbenzamide | HCID 22225830 | — |
Reaction Steps
To a solution 4-chloro-2-fluorobenzoic acid (1 eq) in CH2Cl2 (1.6 M) was added N,O-dimethylhydroxylamine hydrochloride (1.5 eq), EDCI (1.5 eq) and triethylamine (4 eq). The reaction mixture was stirred at rt for 16 hrs, concentrated and 0.5M aqueous citric acid was added. The mixture was extracted with 1:1 EtOAc:Et2O. The combined organic layers were washed with brine, dried over MgSO4 and concentrated to give 4-chloro-2-fluoro-N-methoxy-N-methylbenzamide, which was used as such for the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07019022B2 |
| Source dataset | uspto-grants-2006_03 |
| ORD ID | ord-6d9b38f79a6b434ea99d12e7ca6d779c |
| Source note | uspto-grants-2006_03 |