Diethyl Ether → HCID 73741285, compound

HRID 347607Notes

Reaction equation

HRID 347607 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[N:6]#[O+].[CH:8]([C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1)=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCOCC>C(#N)C>[F:1][B-:2]([F:5])([F:4])[F:3].[CH:8]([C:16]1[CH:17]=[CH:18][C:19]([N+:22]#[N:6])=[CH:20][CH:21]=1)=[CH:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 132654-StyrylphenylamineHCID 11137142Nitrilooxonium tetrafluoroborate

Product 1

HCID 73741285HCID 73741285, compoundYield 324.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
-30 °C

Procedure

To a 25 mL round bottom in a drybox was added nitrosonium tetrafluoroborate (0.11 g, 0.95 mmol). Acetonitrile (2 mL) was added and the flask was cooled down to −30° C. A solution of 4-STYRYLPHENYLAMINE (0.17 g, 0.86 mmol) and BHT (0.19 g, 0.86 mmol) in acetonitrile (5 mL) was added dropwise via syringe. The reaction was allowed to warm to −5° C. over 20 min. Ether (10 mL) was then added and the precipitate was filtered. The title compound was purified by re-precipitating from acetonitrile (3 mL) with ether (15 mL) to yield 0.82 g (34%) of the desired compound.

Workup

  1. temperatureto warm to −5° C. over 20 min
  2. filtrationthe precipitate was filtered
  3. customThe title compound was purified
  4. customby re-precipitating from acetonitrile (3 mL) with ether (15 mL)

Sources & evidence

ORD record
ord-19f7e283f2bb4b389844dbe4f9489af6
Source dataset
uspto-grants-2007_02
Patent number
US07176146B2

Reaction notes

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