Hydrochloric Acid → 5-Chloro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-6-yl-hydrazine

HRID 1871570Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([F:14])([F:13])[O:7][C:8]2([F:12])[F:11])=[CH:4][C:3]=1[Cl:15].[N:16](OS(=O)(=O)O)=O.N([O-])=O.[Na+].S(=O)(=O)(O)O.Cl.[OH-].[Na+]>C(O)(=O)C>[Cl:15][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[NH:1][NH2:16])[C:8]([F:11])([F:12])[O:7][C:6]2([F:14])[F:13]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution wherein 6-amino-5-chloro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran (2.41 g, 10.0 mmol) is in acetic acid (30 ml), a nitrosylsulfuric acid solution prepared from sodium nitrite (760 mg, 11.0 mmol) and concentrated sulfuric acid (5.5 ml) was added dropwise at 10 to 15° C. over a period of about 10 minutes. The reaction solution was then added dropwise into a solution consisting of stannous chloride anhydride (9.5 g) and concentrated hydrochloric acid (8 ml) under vigorous stirring at 0° C. and further stirred for 30 minutes. After a sodium hydroxide solution was added to the reaction mixture to make the solution alkaline, the solution was extracted with diethyl ether, and the organic layer was then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to silica gel column chromatography to give 1.8 g of 5-chloro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-6-yl-hydrazine.

Workup

additionwas added dropwise at 10 to 15° C. over a period of about 10 minutes
additionThe reaction solution was then added dropwise into a solution
stirringfurther stirred for 30 minutes
extractionthe solution was extracted with diethyl ether
dry with materialthe organic layer was then dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-304de17e77634983ab3ea682a19f9f31
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06103750

Reaction notes

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