Water → HCID 11629980, compound

HRID 1666034Notes

Reaction equation

[I-].[CH3:2][S+](C)C.[OH-].[K+].[F:8][C:9]([F:22])([F:21])[C:10]1([C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)[N:12]=[N:11]1.O>C(#N)C>[O:18]1[CH2:2][CH:17]1[C:16]1[CH:19]=[CH:20][C:13]([C:10]2([C:9]([F:8])([F:21])[F:22])[N:11]=[N:12]2)=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

0.95 g of trimethylsulfonium iodide and 0.52 g of potassium hydroxide were dissolved in 4 ml of acetonitrile, and agitated for 10 minutes at 60° C. in a nitrogen gas atmosphere. 1.00 g of 4-(3-trifluoromethyl-3H-diazirine-3-yl)benzaldehyde were added together with 5.3 ml of acetonitrile, then 0.02 g of water were added. This was agitated for one hour at 60° C. in a nitrogen gas atmosphere. After extracting with ethyl ether, the resulting substance was washed twice with water and once with saturated saline solution, then dried with anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the resulting substance was purified by silica gel chromatography (hexane:chloroform=1:2, V/V) to obtain 0.56 g of 3-(4-oxiranylphenyl)-3-trifluoromethyl-3H-diazirine (52% yield).

Workup

stirringThis was agitated for one hour at 60° C. in a nitrogen gas atmosphere
extractionAfter extracting with ethyl ether
washthe resulting substance was washed twice with water and once with saturated saline solution
dry with materialdried with anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was removed under reduced pressure
customthe resulting substance was purified by silica gel chromatography (hexane:chloroform=1:2, V/V)

Sources & evidence

ORD record: ord-982c4896b47741f69dd212f3f7adf5cd
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08043666B2

Reaction notes

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