HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → N-methoxy-N-methylisoxazole-5-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 2-Dimethylaminopyridine | HCID 21885 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | 1,2-Oxazole-5-carboxylic acid | HCID 2060599 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-methoxy-N-methylisoxazole-5-carboxamide | HCID 22489934 | 76% |
Reaction Steps
A solution of isoxazole 5-carboxylic acid (2.81 g), N-methoxy-N-methylamine hydrochloride (2.49 g), EDCI (4.96 g), dimethylaminopyridine (3.15 g) and 4-methylmorpholine (2.8 ml) in dichloromethane (20 ml) was stirred for 18 h. 2M Hydrochloric acid was added and the mixture was extracted with dichloromethane (three times). The organic layers were washed with aqueous sodium hydrogen carbonate and then brine, combined, dried (magnesium sulphate), evaporated and purified by chromatography on silica eluting with petrol-ether to give the sub-title compound as a colourless oil (2.94 g, 76%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06887871B2 |
| Source dataset | uspto-grants-2005_05 |
| ORD ID | ord-25336c835b3447b7b482c43cb98ad6c6 |
| Source note | uspto-grants-2005_05 |