Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | Methyl Acetate | HCID 6584 | — |
| Reactant | Trimethyl orthoformate | HCID 9005 | — |
| Reactant | Sulfolane | HCID 31347 | — |
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | HCID 89704911 | HCID 89704911 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Formic Acid | HCID 284 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Hexamethylphosphoramide | HCID 12679 | — |
| Solvent | 2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- | HCID 81646 | — |
| Product | HCID 89704884 | HCID 89704884 | — |
Reaction Steps
4-Amino-3-fluoro-2-((2-fluorophenyl)amino)-5-hydroxybenzoic acid can be cyclized in the presence of acid (such as p-toluenesulfonic acid, pyridinium toluene-4-sulphonate, formic acid, acetic acid, sulfuric acid) in appropriate solvent (include aliphatic and aromatic hydrocarbon (such as pentane, hexane, heptane, cyclohexane, petroleum ether, petrol, gasoline, benzene, toluene, xylene), aliphatic and aromatic halo-hydrocarbon (such as dichloromethane, 1,2-dichloroethane, chloroform, phenixin, chlorobenzene, o-dichlorobenzene), ether (such as diethyl ether, dibutyl ether, glycol dimethyl ether, 2-methoxyethyl ether, tetrahydrofuran, dioxane), ketone (such as acetone, methyl ethyl ketone, methyl isopropyl ketone, methyl isobutyl ketone), ester (such as ethyl acetate, methyl acetate), nitrile (such as acetonitrile, propiononitrile), amide (such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidin-2-one), DMSO, sulfolane, HMPA, DMPU, prefer methyl acetate, ethyl acetate and trimethoxymethane) for some time (0.2-12 h, prefer 0.5-10 h). 4-Fluoro-5-((2-fluorophenyl)amino)benzo[d]oxazole-6-carboxylic acid is obtained after conventional workup.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09290468B2 |
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| Source dataset | uspto-grants-2016_03 |
|---|
| ORD ID | ord-0be8d8e5aa9e43cba22d00003ef46bbe |
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| Source note | uspto-grants-2016_03 |
|---|