Hydrochloric Acid → HCID 58028470, compound

HRID 2408313Notes

Reaction equation

HRID 2408313 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([N:12]([C:50]2[C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[CH:53]=[CH:52][CH:51]=2)[C:13]2[CH:25]=[CH:24][C:23]3[C:22]4[C:17](=[CH:18][C:19]([N:26]([C:37]5[CH:42]=[CH:41][CH:40]=[C:39]([CH:43]6OCC[O:44]6)[CH:38]=5)[C:27]5[C:36]6[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=6)[CH:30]=[CH:29][CH:28]=5)=[CH:20][CH:21]=4)[C:16]([CH3:49])([CH3:48])[C:15]=3[CH:14]=2)[CH:9]=[CH:10][CH:11]=1.Cl>CC(C)=O>[CH3:48][C:16]1([CH3:49])[C:17]2[CH:18]=[C:19]([N:26]([C:37]3[CH:38]=[C:39]([CH:40]=[CH:41][CH:42]=3)[CH:43]=[O:44])[C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=[CH:29][CH:28]=3)[CH:20]=[CH:21][C:22]=2[C:23]2[C:15]1=[CH:14][C:13]([N:12]([C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[CH:2]=[O:1])[C:50]1[C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[CH:53]=[CH:52][CH:51]=1)=[CH:25][CH:24]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58028464N2,N7-bis(3-(1,3-dioxolan-2-yl)phenyl)-9,9-dimethyl-N2,N7-di(naphthalen-1-yl)-9H-fluorene-2,7-diamine

Product 1

HCID 58028470HCID 58028470, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a three-neck round-bottom flask, were added 8.0 g N2,N7-bis(3-(1,3-dioxolan-2-yl)phenyl)-9,9-dimethyl-N2,N7-di(naphthalen-1-yl)-9H-fluorene-2,7-diamine and in 100 mL acetone. 41.1 mL 2 M hydrochloric acid solution was added slowly to the reaction mixture through an addition funnel. After TLC showed the reaction was done, the solvent was removed by evaporation. 200 mL Ethyl acetate was added, and the reaction mixture was extracted using DI water (4×200 mL). The organic layer was dried over sodium sulfate. After filtration, the solvent was removed by evaporation. The product (6.9 g) was obtained after drying under vacuum, and was carried on to next step without further purification. The structure was confirmed by NMR.

Workup

  1. customthe solvent was removed by evaporation
  2. addition200 mL Ethyl acetate was added
  3. extractionthe reaction mixture was extracted
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-b5001a5d5ac24e8cabf07e41d1310ce2
Source dataset
uspto-grants-2014_08
Patent number
US08815639B2

Reaction notes

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