Sulfuric Acid → HCID 89704884, compound

HRID 928936Notes

Reaction equation

HRID 928936 reaction equation
[NH2:1][C:2]1[C:10]([OH:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[C:3]=1[F:20].[C:21]1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.S(=O)(=O)(O)O.S1(CCCC1)(=O)=O.C(OC)(=O)C.COC(OC)OC>C(OCC)(=O)C.CN1C(=O)N(C)CCC1.CN(P(N(C)C)(N(C)C)=O)C.CS(C)=O.CCOCC.C(O)(=O)C.C(O)=O>[F:20][C:3]1[C:2]2[N:1]=[CH:21][O:11][C:10]=2[CH:9]=[C:5]([C:6]([OH:8])=[O:7])[C:4]=1[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19]

Participants

15

Reactant 7

HCID 1118Sulfuric AcidHCID 6101p-Toluenesulfonic acidHCID 6584Methyl AcetateHCID 9005Trimethyl orthoformateHCID 31347SulfolaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 89704911HCID 89704911, compound

Product 1

HCID 89704884HCID 89704884, compound

Reagents, catalysts & solvents 7

HCID 176Acetic AcidSolventHCID 284Formic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolventHCID 12679HexamethylphosphoramideSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

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.

Sources & evidence

ORD record
ord-0be8d8e5aa9e43cba22d00003ef46bbe
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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