Aniline → 1,2,4,6-Tetraphenylpyridin-1-ium tetrafluoroborate

HRID 606553Notes

Reaction equation

HRID 606553 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[C:6]1([C:12]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:15]=[C:14]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O+]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(O)C>[F:1][B-:2]([F:5])([F:4])[F:3].[C:31]1([N+:30]2[C:12]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:17][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][C:14]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 9930615Pyrylium, 2,4,6-triphenyl-, tetrafluoroborate(1-)

Product 1

HCID 126655461,2,4,6-Tetraphenylpyridin-1-ium tetrafluoroborateYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 500 mL round-bottomed flask equipped with a condenser was charged with 2,4,6-triphenyl-pyrylium tetrafluoroborate (22.4 g, 0.056 mole), aniline (5.8 g, 0.060 mole) and ethanol (200 mL). The resulting solution was magnetically stirred and refluxed under a nitrogen atmosphere for 6 hours. The solution was cooled to room temperature, and the product 27 precipitated as greenish-yellow, crystalline solid. The product was collected by filtration and dried in a vacuum oven at 100° C. (23 g, 87% yield). Mp=253° C.

Workup

  1. customA 500 mL round-bottomed flask equipped with a condenser
  2. temperaturerefluxed under a nitrogen atmosphere for 6 hours
  3. customthe product 27 precipitated as greenish-yellow, crystalline solid
  4. filtrationThe product was collected by filtration
  5. customdried in a vacuum oven at 100° C. (23 g, 87% yield)

Sources & evidence

ORD record
ord-682788a548194c61998a1337d51cc3c6
Source dataset
uspto-grants-2011_03
Patent number
US07915332B2

Reaction notes

Loading…