Sodium hexafluoroantimonate → HCID 86600078, compound

HRID 2373135Notes

Reaction equation

HRID 2373135 reaction equation
[O-]S(C(F)(F)F)(=O)=O.[CH2:9]([C:13]1[CH:18]=[CH:17][C:16]([N:19]([C:29]2[CH:34]=[CH:33][C:32](/[CH:35]=[CH:36]/[C:37]3[CH:42]=[CH:41][C:40]([N:43]([C:53]4[CH:58]=[CH:57][C:56]([CH2:59][CH2:60][CH2:61][CH3:62])=[CH:55][CH:54]=4)[C:44]4[CH:49]=[CH:48][CH:47]=[C:46]([S+:50]([CH3:52])[CH3:51])[CH:45]=4)=[CH:39][CH:38]=3)=[CH:31][CH:30]=2)[C:20]2[CH:21]=[C:22]([S+:26]([CH3:28])[CH3:27])[CH:23]=[CH:24][CH:25]=2)=[CH:15][CH:14]=1)[CH2:10][CH2:11][CH3:12].[O-]S(C(F)(F)F)(=O)=O.[F:71][Sb-:72]([F:77])([F:76])([F:75])([F:74])[F:73].[Na+]>CC(C)=O>[F:71][Sb-:72]([F:77])([F:76])([F:75])([F:74])[F:73].[CH2:9]([C:13]1[CH:14]=[CH:15][C:16]([N:19]([C:29]2[CH:34]=[CH:33][C:32]([CH:35]=[CH:36][C:37]3[CH:42]=[CH:41][C:40]([N:43]([C:53]4[CH:58]=[CH:57][C:56]([CH2:59][CH2:60][CH2:61][CH3:62])=[CH:55][CH:54]=4)[C:44]4[CH:49]=[CH:48][CH:47]=[C:46]([S+:50]([CH3:52])[CH3:51])[CH:45]=4)=[CH:39][CH:38]=3)=[CH:31][CH:30]=2)[C:20]2[CH:21]=[C:22]([S+:26]([CH3:28])[CH3:27])[CH:23]=[CH:24][CH:25]=2)=[CH:17][CH:18]=1)[CH2:10][CH2:11][CH3:12].[F:71][Sb-:72]([F:77])([F:76])([F:75])([F:74])[F:73]

Participants

4

Reactant 2

HCID 16689647Sodium hexafluoroantimonateHCID 86600079HCID 86600079, compound

Product 1

HCID 86600078HCID 86600078, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Trans-[3-((4-butylphenyl){4-[2-(4- {(4-butylphenyl)[3-(dimethylsulfonio)phenyl]amino}phenyl)vinyl]phenyl}amino)phenyl](dimethyl)sulfonium triflate (19) (0.87 g, 0.83 mmol) was dissolved in acetone (20 ml). To this solution was added 20 ml of an aqueous solution of sodium hexafluoroantimonate (0.88 g, 3.40 mmol). The resultant mixture was stirred two days in the dark at room temperature; with slow evaporation of acetone, a yellow solid was formed and collected by filtration. The yellow solid was washed four times with water and three times with ether. A NMR-pure product was obtained without further purification and isolated in 93.8% (0.95 g) yield. 1H NMR (CD3COCD3, 500 MHz) δ ppm: 7.1-7.4 (m, 24 Ar—H, 2 ═CH), 3.06 (s, 6H, CH3,) 2.72 (t, J=7.7 Hz, CH2, 4H), 1.71 (m, CH2, 4H), 1.46 (m, CH2, 4H), 1.04 (t, J=7.3 Hz, CH3, 6H)

Workup

  1. customwith slow evaporation of acetone
  2. customa yellow solid was formed
  3. filtrationcollected by filtration
  4. washThe yellow solid was washed four times with water and three times with ether
  5. customA NMR-pure product was obtained without further purification
  6. customisolated in 93.8% (0.95 g)
  7. customyield

Sources & evidence

ORD record
ord-08cfdb1a527740fcb487f8bf51c29a92
Source dataset
uspto-grants-2008_12
Patent number
US07459106B2

Reaction notes

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