Sodium hexafluoroantimonate → HCID 86600080, compound

HRID 2373136Notes

Reaction equation

[O-]S(C(F)(F)F)(=O)=O.[CH2:9]([C:13]1[CH:18]=[CH:17][C:16]([N:19]([C:35]2[CH:40]=[CH:39][C:38](/[CH:41]=[CH:42]/[C:43]3[CH:48]=[CH:47][C:46]([N:49]([C:65]4[CH:70]=[CH:69][C:68]([CH2:71][CH2:72][CH2:73][CH3:74])=[CH:67][CH:66]=4)[C:50]4[CH:55]=[CH:54][CH:53]=[C:52]([SH+:56][CH2:57][CH2:58][C:59]5[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=5)[CH:51]=4)=[CH:45][CH:44]=3)=[CH:37][CH:36]=2)[C:20]2[CH:21]=[C:22]([SH+:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[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:83][Sb-:84]([F:89])([F:88])([F:87])([F:86])[F:85].[Na+]>CC(C)=O>[F:83][Sb-:84]([F:89])([F:88])([F:87])([F:86])[F:85].[CH2:71]([C:68]1[CH:67]=[CH:66][C:65]([N:49]([C:46]2[CH:47]=[CH:48][C:43](/[CH:42]=[CH:41]/[C:38]3[CH:39]=[CH:40][C:35]([N:19]([C:16]4[CH:17]=[CH:18][C:13]([CH2:9][CH2:10][CH2:11][CH3:12])=[CH:14][CH:15]=4)[C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([SH+:26][CH2:27][CH2:28][C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)[CH:21]=4)=[CH:36][CH:37]=3)=[CH:44][CH:45]=2)[C:50]2[CH:51]=[C:52]([SH+:56][CH2:57][CH2:58][C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)[CH:53]=[CH:54][CH:55]=2)=[CH:70][CH:69]=1)[CH2:72][CH2:73][CH3:74].[F:83][Sb-:84]([F:89])([F:88])([F:87])([F:86])[F:85]

Participants

Conditions

Temperature: 0 °C

Procedure

trans-[3-((4-butylphenyl){4-[2-(4-{(4-butylphenyl)[3-((benzyl)methylsulfonio)phenyl]amino}phenyl)vinyl]phenyl}amino)phenyl]((benzyl)methyl)sulfonium triflate (20) (0.85 g 0.81 mmol) was dissolved in acetone (10 ml). To this solution was added 10 ml of an aqueous solution of sodium hexafluoroantimonate (0.84 g, 3.25 mmol). The resultant mixture was stirred two days with slow evaporation of acetone in the dark at room temperature. The mixture was allowed to cool at 0° C., the yellow oil that formed solidified. The yellow solid was collected by filtration and washed four times with water and three times with ether. NMR-pure product was obtained without further purification in 83.2% yield (0.85 g). 1H NMR (CD3COCD3, 500 MHz) δ ppm: 6.9-7.7 (m, 36H, 34 Ar—H, 2 ═CH), 5.27 (d, 2J=12.5 Hz, 2H, SCH2), 5.02 (d, 2J=12.5 Hz, 2H, SCH2), 3.52 (s, 6H, CH3), 2.63 (t, J=7.7 Hz, CH2, 4H), 1.61 (m, CH2, 4H), 1.36 (m, CH2, 4H), 0.95 (t, J=7.2 Hz, CH3, 6H)13 C NMR (CD3COCD3, 125.7 MHz) δppm: 149.3, 145.6, 143.5, 139.9, 133.5, 131.9, 130.7, 130.0, 129.8, 129.3, 127.9, 127.7, 127.1, 126.5, 125.6, 124.5, 123.8, 123.4, 121.7, 51.0, 34.7, 33.5, 24.5, 22.1, 13.3.

Workup

customthe yellow oil that formed
filtrationThe yellow solid was collected by filtration
washwashed four times with water and three times with ether
customNMR-pure product was obtained without further purification in 83.2% yield (0.85 g)

Sources & evidence

ORD record: ord-1ccfa20b304041a5a551b2cc18a61144
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459106B2

Reaction notes

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