HuagongsheHuagongshe Chemistry Print Report · For research reference only
Formic Acid → 2-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]oxyacetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | tert-butyl 2-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]oxyacetate | HCID 87403035 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]oxyacetic acid | HCID 46701801 | 80% |
Reaction Steps
A solution of [1-{4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-phenyl}-meth-(E)-ylideneaminooxy]-acetic acid tert-butyl ester (i.e the product of Step 1, 531 mg) in CH2Cl2 (20 mL) was treated with formic acid (0.25 mL, 0.30 g) and stirred at room temperature over night. Trifluoroacetic acid (0.50 g) was added and the mixture stirred until tlc (thin layer chromatography) indicated completion of the reaction. The organic layer was washed with water three times, dried (Na2SO4) and evaporated to give the title compound (502 mg, 80%) that was used in the next step without further purification. NMR indicated the absence of the tert butyl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08722673B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-25f165343bd8469c91d255123743b6ea |
| Source note | uspto-grants-2014_05 |