Sodium Hydroxide → HCID 131733080, compound

HRID 2179833Notes

Reaction equation

HRID 2179833 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH2:12]([N+:16]1[C:24]2[CH:23]=[CH:22][C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[C:19]=2[C:18]([CH3:30])([CH3:29])[C:17]=1[CH:31]=[CH:32][C:33]1[CH2:37][CH2:36][C:35](=[CH:38][CH:39]=[C:40]2[C:48]([CH3:50])([CH3:49])[C:47]3[C:46]4[CH:51]=[CH:52][CH:53]=[CH:54][C:45]=4[CH:44]=[CH:43][C:42]=3[N:41]2[CH2:55][CH2:56][CH2:57][CH3:58])[C:34]=1[S:59]([C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)(=[O:61])=[O:60])[CH2:13][CH2:14][CH3:15].[C-:68]([S:83]([C:86]([F:89])([F:88])[F:87])(=[O:85])=[O:84])([S:76]([C:79]([F:82])([F:81])[F:80])(=[O:78])=[O:77])[S:69]([C:72]([F:75])([F:74])[F:73])(=[O:71])=[O:70].[OH-].[Na+]>O.C(C(C)=O)C(C)C>[C-:68]([S:69]([C:72]([F:75])([F:73])[F:74])(=[O:71])=[O:70])([S:83]([C:86]([F:87])([F:88])[F:89])(=[O:84])=[O:85])[S:76]([C:79]([F:82])([F:81])[F:80])(=[O:77])=[O:78].[CH2:12]([N+:16]1[C:24]2[CH:23]=[CH:22][C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[C:19]=2[C:18]([CH3:29])([CH3:30])[C:17]=1[CH:31]=[CH:32][C:33]1[CH2:37][CH2:36][C:35](=[CH:38][CH:39]=[C:40]2[C:48]([CH3:49])([CH3:50])[C:47]3[C:46]4[CH:51]=[CH:52][CH:53]=[CH:54][C:45]=4[CH:44]=[CH:43][C:42]=3[N:41]2[CH2:55][CH2:56][CH2:57][CH3:58])[C:34]=1[S:59]([C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1)(=[O:61])=[O:60])[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4306513HCID 4306513, compound2×HCID 86658629HCID 86658629, compound

Product 1

HCID 131733080HCID 131733080, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 1.86 g (2 mmol) of 3-butyl-2-(2-{3-[2-(3-butyl-1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene)-ethylidene]-2-(phenylsulfonyl)cyclopent-1-en-1-yl}ethenyl)-1,1-dimethyl-1H-benzo[e]indol-3-ium p-toluenesulfonate, 2.21 g (3 mmol) of a 56% tris(trifluoromethanesulfonyl)methide acid aqueous solution, 0.48 g of a 25% sodium hydroxide aqueous solution, 30 g of water, and 30 g of methyl isobutyl ketone was stirred for 8 hours at room temperature, whereupon the organic layer was taken out. The organic layer was combined with 0.74 g (1 mmol) of a 56% tris(trifluoromethanesulfonyl)methide acid aqueous solution and 30 g of water and stirred overnight, whereupon the organic layer was taken out. The organic layer was washed with water and concentrated in vacuum. Diisopropyl ether was added to the residue for recrystallization. The crystal was collected and dried in vacuum, obtaining the target compound, 3-butyl-2-(2-{3-[2-(3-butyl-1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene)ethylidene]-2-(phenylsulfonyl)cyclopent-1-en-1-yl}ethenyl)-1,1-dimethyl-1H-benzo[e]indol-3-ium tris(trifluoromethylsulfonyl)methide. Brown crystal, 2.2 g, yield 92%.

Workup

  1. stirringstirred overnight, whereupon the organic layer
  2. washThe organic layer was washed with water
  3. concentrationconcentrated in vacuum
  4. additionDiisopropyl ether was added to the residue for recrystallization
  5. customThe crystal was collected
  6. customdried in vacuum

Sources & evidence

ORD record
ord-8439f5cbb41b4efb8c9f97012fb59b2c
Source dataset
uspto-grants-2015_06
Patent number
US09069245B2

Reaction notes

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