Hydrochloric Acid → HCID 15037285, compound

HRID 1607433Notes

Reaction equation

HRID 1607433 reaction equation
[F:1][C:2]1[CH:14]=[C:13]([F:15])[C:12]2[C:11]3[C:6](=[CH:7][C:8]([F:19])=[CH:9][C:10]=3[N+]([O-])=O)[CH2:5][C:4]=2[CH:3]=1.C1(=[O:33])C2C(C3C(C=2)=CC=CC=3)=CC=C1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].NC1C=C(F)C=C2C=1C1C(=C2)C(=O)C(F)=CC=1F.[Sn](Cl)Cl.Cl.N([O-])=O.[Na+].[H+].[B-](F)(F)(F)F.[O:77]([CH2:81][CH3:82])[C:78]([S-:80])=[S:79].[K+]>C(O)(=O)C.O1CCCC1.C1(C)C=CC=CC=1.O.C(O)C>[O:77]([CH2:81][CH3:82])[C:78]([S:80][C:10]1[CH:9]=[C:8]([F:19])[CH:7]=[C:6]2[C:11]=1[C:12]1[C:13]([F:15])=[CH:14][C:2]([F:1])=[CH:3][C:4]=1[C:5]2=[O:33])=[S:79]

Participants

15

Reactant 9

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 25408Sodium DichromateHCID 28118Tetrafluoroboric acidHCID 2735045Potassium ethylxanthateHCID 15037282HCID 15037282, compoundHCID 22281833FluoreneoneHCID 23668193Sodium NitriteHCID 67903265HCID 67903265, compound

Product 1

HCID 15037285HCID 15037285, compound

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,4,7-Trifluoro-5-nitrofluorene was oxidized to the fluorenone using sodium dichromate in acetic acid and then reduced to 5-amino-2,4,7-trifluorofluorenone using tin(II)chloride in a mixturre of ethanol and concentrated hydrochloric acid. The amine was converted to the 5-diazonium tetrafluoroborate salt by treatment with sodium nitrite in a mixture of tetrahydrofuran and aqueous fluoboric acid. The material was allowed to react with potassium ethyl xanthate in a hot mixture of water and toluene to provide ethyl 2,4,7-trifluoro-9-oxofluoren-5-yl xanthate which was then hydrolyzed using ethanolic sodium hydroxide and S-methylated with methyl iodide to give 2,4,7-tri-fluoro-5-methylthiofluorenone. Hydantoin formation was accomplished by heating an ethanol solution of the ketone, potassium cyanide, ammonium carbonate at 115° C. for 15 hours.

Sources & evidence

ORD record
ord-767987ca8c8c4a1d9eb7773632fc5d0b
Source dataset
uspto-grants-1989_09
Patent number
US04864028

Reaction notes

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