HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → N-(2,4-Dichloropyrimidin-5-yl)-4-methoxy-3,5-dimethylbenzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 5-Amino-2,4-dichloropyrimidine | HCID 257797 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 3,5-Dimethyl-4-methoxybenzoyl chloride | HCID 21435383 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | N-(2,4-Dichloropyrimidin-5-yl)-4-methoxy-3,5-dimethylbenzamide | HCID 86675952 | 43% |
Reaction Steps
3.2 g of 5-amino-2,4-dichloropyrimidine in 50 ml ethyl acetate were added to a mixture of 25 ml of saturated aqueous sodium bicarbonate solution and 25 ml of water. At room temperature, a solution of 4.9 g of 3,5-dimethyl-4-methoxybenzoyl chloride was added over a period of 15 min. The mixture was stirred intensively for 4 h. The layers were then separated, after which the aqueous layer was extracted twice with ethyl acetate. After drying over sodium sulfate and filtration, the solvent was removed under reduced pressure, giving 7.54 g of crude product. The crude product was triturated with 25 ml of isopropanol. Filtration and washing with 10 ml of isopropanol gave 2.74 g of the title compound in the form of a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08735402B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-dc6020ee77a54ed0866f1ee00978042f |
| Source note | uspto-grants-2014_05 |