Potassium Carbonate → HCID 14698845, compound

HRID 1165379Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[NH:14][N:13]=[N:12]1.C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:28][CH2:29][CH2:30][F:31])(=O)=O>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[N:14]([CH2:28][CH2:29][CH2:30][F:31])[N:13]=[N:12]1

Participants

Conditions

Temperature: 60 °C

Procedure

A stirred mixture of 28.0 g (0.124 mole) of 1-(2-fluoro-4-nitrophenyl)-1,4-dihydro-5H-tetrazol-5-one, 19.3 g (0.140 mole) of potassium carbonate, and 21.8 g (0.140 mole) of 3-fluoropropyl methanesulfonate in 100 mL of dimethylformamide was heated at 60° C. for approximately 18 hours. The reaction mixture was poured into icewater, and the resultant fixture was extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate and was filtered. The filtrate was evaporated under reduced pressure leaving a residue. This residue was purified by column chromatography on silica gel, eluting with methylene chloride, to yield 21.5 g of 1-(2-fluoro-4-nitrophenyl)-4-(3-fluoropropyl)-1,4-dihydro-5H-tetrazol-5-one as a solid, m.p. 86°-89° C.

Workup

additionThe reaction mixture was poured into icewater
extractionthe resultant fixture was extracted with diethyl ether
dry with materialThe extract was dried over anhydrous magnesium sulfate
filtrationwas filtered
customThe filtrate was evaporated under reduced pressure
customleaving a residue
customThis residue was purified by column chromatography on silica gel
washeluting with methylene chloride

Sources & evidence

ORD record: ord-f7f257496556401c919b7d8190cb6cbe
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04909829

Reaction notes

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