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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 928936Generated: October 31, 2026

Sulfuric Acid → HCID 89704884, compound

https://huagongshe.com/reaction/928936

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSulfuric AcidHCID 1118—
Reactantp-Toluenesulfonic acidHCID 6101—
ReactantMethyl AcetateHCID 6584—
ReactantTrimethyl orthoformateHCID 9005—
ReactantSulfolaneHCID 31347—
ReactantBenzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 466102—
ReactantHCID 89704911HCID 89704911—
SolventAcetic AcidHCID 176—
SolventFormic AcidHCID 284—
SolventDimethyl SulfoxideHCID 679—
SolventDiethyl EtherHCID 3283—
SolventEthyl AcetateHCID 8857—
SolventHexamethylphosphoramideHCID 12679—
Solvent2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 81646—
ProductHCID 89704884HCID 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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09290468B2
Source datasetuspto-grants-2016_03
ORD IDord-0be8d8e5aa9e43cba22d00003ef46bbe
Source noteuspto-grants-2016_03