Dimethyl Sulfoxide → HCID 58977994, compound

HRID 1179300Notes

Reaction equation

F[C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.CS(C)=O.CCN(C(C)C)C(C)C.[Cl-].[CH3:24][N:25]([CH3:32])[S:26]([CH2:29][CH2:30][NH3+:31])(=[O:28])=[O:27]>CCOC(C)=O>[C:8]([C:3]1[C:2]([NH:31][CH2:30][CH2:29][S:26]([N:25]([CH3:32])[CH3:24])(=[O:28])=[O:27])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:9]

Participants

Conditions

Temperature: 80 °C

Procedure

3-fluoro-2-cyanopyridine (Sakamoto et. al., Chem. Pharm. Bull. 1985, 33: 565-571) (1 g, 8.2 mmol) was placed in a high pressure tube equipped with a stir bar. DMSO (7 mL), Hunig's base (1.57 mL, 9.0 mmol) and 2-[(dimethylamino)sulfonyl]-ethanaminium chloride (1.7 g, 9.0 mmol) were added and the vessel was sealed and heated to 80° C. for 5.5 hours, then stirred at room temperature overnight. The reaction was treated with an additional 0.3 equivalent of Hunig's base and 0.2 equivlanet of the amine salt and heated for 3 hours, but the reaction progressed no further. The mixture was cooled, added to the top of a silica gel column (60 mm by 7 inches) packed in EtOAc and the column eluted with EtOAc. Careful cutting of fractions allowed isolation of the product after evaporation as a clear, colorless oil that solidified upon standing.

Workup

customequipped with a stir bar
customthe vessel was sealed
temperatureheated for 3 hours
temperatureThe mixture was cooled
additionadded to the top of a silica gel column (60 mm by 7 inches)
washthe column eluted with EtOAc
customafter evaporation as a clear, colorless oil that

Sources & evidence

ORD record: ord-554a4f8014bd43098d704e856d0f18c8
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279487B2

Reaction notes

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