Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | 5-Methyl-3-phenylisoxazole-4-carboxaldehyde | HCID 2776144 | — |
| Reactant | Ethyl 2-methyl-1,3-thiazole-5-carboxylate | HCID 12808791 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 66643683 | HCID 66643683 | 19.2% |
Reaction Steps
2-Methyl-thiazole-5-carboxylic acid ethyl ester (547 mg, 2.92 mmol) was dissolved in acetic anhydride (0.15 mL, 15.5 mmol) and acetic acid (0.04 mL, 2.54 mmol) then 5-methyl-3-phenyl-4-isoxazolecarbaldehyde (500 mg, 2.92 mmol) was added and the reaction mixture warmed to 120° C. After 6 days, the reaction mixture was cooled to room temperature then diluted with water and extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated then purified by chromatography (silica, 0 to 30% ethyl acetate in heptane) to give the title compound (191 mg, 19%) as an off-white solid after trituration with isopropylether. MS: m/e=341.3 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08178522B2 |
|---|
| Source dataset | uspto-grants-2012_05 |
|---|
| ORD ID | ord-44193f3d90e4415c8471e640b89b2615 |
|---|
| Source note | uspto-grants-2012_05 |
|---|
