Sodium hexafluoroantimonate → HCID 86600076, compound

HRID 2373134Notes

Reaction equation

HRID 2373134 reaction equation
[O-]S(C(F)(F)F)(=O)=O.[CH3:9][S+:10]([CH3:54])[C:11]1[CH:12]=[C:13]([N:17]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26]3[CH:31]=[CH:30][C:29]([N:32]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[C:33]4[CH:34]=[C:35]([S+:39]([CH3:41])[CH3:40])[CH:36]=[CH:37][CH:38]=4)=[CH:28][CH:27]=3)=[CH:20][CH:19]=2)[CH:14]=[CH:15][CH:16]=1.[O-]S(C(F)(F)F)(=O)=O.[F:63][Sb-:64]([F:69])([F:68])([F:67])([F:66])[F:65].[Na+]>C(Cl)Cl.CC(C)=O>[F:63][Sb-:64]([F:69])([F:68])([F:67])([F:66])[F:65].[CH3:41][S+:39]([CH3:40])[C:35]1[CH:34]=[C:33]([N:32]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:29]2[CH:28]=[CH:27][C:26]([CH:25]=[CH:24][C:21]3[CH:22]=[CH:23][C:18]([N:17]([C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)[C:13]4[CH:12]=[C:11]([S+:10]([CH3:9])[CH3:54])[CH:16]=[CH:15][CH:14]=4)=[CH:19][CH:20]=3)=[CH:31][CH:30]=2)[CH:38]=[CH:37][CH:36]=1.[F:63][Sb-:64]([F:69])([F:68])([F:67])([F:66])[F:65]

Participants

5

Reactant 2

HCID 16689647Sodium hexafluoroantimonateHCID 86600077HCID 86600077, compound

Product 1

HCID 86600076HCID 86600076, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

trans-{3-[[4-(2-{4-[[3-(dimethylsulfonio)phenyl](phenyl)amino]phenyl}vinyl)phenyl](phenyl)amino]phenl}(dimethyl)sulfonium triflate (17) (0.3 g 0.33 mmol) was dissolved in methylene chloride (5 ml) and acetone (10 ml). To this solution was added 10 ml aqueous sodium hexafluoroantimonate solution (0.341 g, 1.32 mmol). The resultant mixture was stirred three days in the dark at room temperature with slow evaporation of methylene chloride and acetone, a yellow solid was formed and collected by filtration. The yellow solid was washed four times with water and three times with ether. NMR-pure product was obtained without further purification in 75.4% (0.31 g) yield. 1H NMR (DMSO, 500 MHz) δ ppm: 7.0-7.6 (m, 26H, Ar—H), 7.16 (s, ═CH, 2H), 3.35 (s, CH3, 12H) Anal. calcd for C44H40N2S2Sb2F12: C, 45.51; H, 3.64; N, 2.53; S, 5.78.

Workup

  1. customwith slow evaporation of methylene chloride and 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. customNMR-pure product was obtained without further purification in 75.4% (0.31 g)
  6. customyield

Sources & evidence

ORD record
ord-08a9acc61bcd4271ab7ea3f6da6f4a90
Source dataset
uspto-grants-2008_12
Patent number
US07459106B2

Reaction notes

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