Stannous chloride dihydrate → HCID 76624961, compound

HRID 1671845Notes

Reaction equation

HRID 1671845 reaction equation
[CH2:1]([O:13][C:14]1[CH:15]=[C:16]([CH:33]=[CH:34][C:35]2[CH:96]=[CH:95][C:38]3[C:39]4[C:48]([C:49]5[CH:54]=[CH:53][C:52]([CH:55]=[CH:56][C:57]6[CH:62]=[CH:61][C:60]([O:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])=[C:59]([O:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH3:88])[CH:58]=6)=[CH:51][C:50]=5[C:37]=3[CH:36]=2)=[N:47][C:46]2[C:41](=[CH:42][C:43]([N+:92]([O-])=O)=[C:44]([N+:89]([O-])=O)[CH:45]=2)[N:40]=4)[CH:17]=[CH:18][C:19]=1[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O.O.Cl[Sn]Cl>O=O>[CH2:1]([O:13][C:14]1[CH:15]=[C:16]([CH:33]=[CH:34][C:35]2[CH:96]=[CH:95][C:38]3[C:39]4[C:48]([C:49]5[CH:54]=[CH:53][C:52]([CH:55]=[CH:56][C:57]6[CH:62]=[CH:61][C:60]([O:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])=[C:59]([O:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH3:88])[CH:58]=6)=[CH:51][C:50]=5[C:37]=3[CH:36]=2)=[N:47][C:46]2[C:41](=[CH:42][C:43]([NH2:92])=[C:44]([NH2:89])[CH:45]=2)[N:40]=4)[CH:17]=[CH:18][C:19]=1[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 76624947HCID 76624947, compound

Product 1

HCID 76624961HCID 76624961, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 977OxygenSolvent2×

Conditions

Temperature
70 °C

Procedure

This compound was synthesized according to a modified literature procedure.52 A Schlenk tube was charged with 3,6-Bis-[2-(3,4-bis-dodecyloxy-phenyl)-vinyl]-11,12-dinitro-dibenzo[a,c]-phenazine BRK_III—63A (564 mg, 0.43 mmol) and (970 mg, 4.30 mmol) of SnCl2.2H2O and was subjected to vacuum. Under N2, 30 ml of O2-free ethanol was transferred to the reaction mixture, which was heated at 70° C. The color of the reaction mixture did not change after one hour and TLC did not show the conversion of the starting material. Additional 50 ml of O2-free ethanol was added and the mixture was refluxed for 23 hours. The reaction was allowed to cool down to room temperature and was then dropped over ice. The solution was extracted with 3×150 ml of ether. The ether extracts were combined and were dried over MgSO4 and was filtered. The solvent (solution is blue fluorescent) was evaporated under vacuum to yield 122 mg (23% yield) of brown solid. HRMS-MALDI-TOF (M+H): m/z 1251.9535; calcd for C84H123N4O4, 1251.9539.

Workup

  1. customThis compound was synthesized
  2. temperaturethe mixture was refluxed for 23 hours
  3. temperatureto cool down to room temperature
  4. additionwas then dropped over ice
  5. extractionThe solution was extracted with 3×150 ml of ether
  6. dry with materialwere dried over MgSO4
  7. filtrationwas filtered
  8. customThe solvent (solution is blue fluorescent) was evaporated under vacuum

Sources & evidence

ORD record
ord-09ca71a109d148df9cf3c366e4b52194
Source dataset
uspto-grants-2011_08
Patent number
US07994423B2

Reaction notes

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