1,10-Phenanthroline → HCID 53997763, compound

HRID 1288676Notes

Reaction equation

HRID 1288676 reaction equation
[C:1]1([N:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([N:40]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:36][CH:35]=2)=[CH:30][CH:29]=1.N1[C:66]2[C:57](=[CH:58][CH:59]=[C:60]3[C:65]=2[N:64]=[CH:63][CH:62]=[CH:61]3)C=CC=1.[OH-].[K+]>C1(C)C(C)=CC=CC=1>[C:1]1([N:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:20]=[CH:19][C:17]([N:18]([C:17]4[CH:19]=[CH:20][C:14]([C:11]5[CH:12]=[CH:13][C:8]([N:64]([C:65]6[CH:66]=[CH:57][CH:58]=[CH:59][CH:60]=6)[C:63]6[CH:62]=[CH:61][CH:6]=[CH:1][CH:2]=6)=[CH:9][CH:10]=5)=[CH:15][CH:16]=4)[C:28]4[CH:33]=[CH:32][C:31]([C:34]5[CH:39]=[CH:38][C:37]([N:40]([C:47]6[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=6)[C:41]6[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=6)=[CH:36][CH:35]=5)=[CH:30][CH:29]=4)=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 13181,10-PhenanthrolineHCID 14797Potassium HydroxideHCID 218488984'-Iodo-N,N-diphenyl[1,1'-biphenyl]-4-amineHCID 22715221HCID 22715221, compound

Product 1

HCID 53997763HCID 53997763, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A 250 milliliter 3-necked round bottom flask equipped with a mechanical stirrer, reflux condenser, and argon inlet was purged with argon and then charged with N,N-diphenylbenzidine (4.95 grams, 0.0147 mol), 4'-iodo-N, N-diphenyl-4-aminobiphenyl (11.0 grams, 0.0246 mol), xylene (15 milliliters), 1,10-phenanthroline (0.22 gram, 1.22 mmol), cuprous chloride (0.122 gram, 1.22 mmol), and potassium hydroxide flakes (11.04 grams, 0.197 mol). Under an argon atmosphere, the reaction mixture was heated to reflux with an oil bath and allowed to proceed at that temperature until chromatographic analysis indicated that the reaction was complete after approximately 6 hours. The oil bath was removed and 100 milliliters of toluene and 20 milliliters of water were then added with efficient stirring. The resulting two phase mixture was transferred into a separatory funnel and the layers separated. The organic phase was washed with water and treated under argon with 25 grams of alumina. After the alumina was filtered off, the organic phase was evaporated to remove the toluene. The above product compound was obtained by recrystallization of the residue from cyclohexane. Yield: 6.9 grams. m.p. 283.97° C., Tg 141° C.

Workup

  1. customA 250 milliliter 3-necked round bottom flask equipped with a mechanical stirrer
  2. temperaturereflux condenser, and argon inlet
  3. customwas purged with argon
  4. temperatureUnder an argon atmosphere, the reaction mixture was heated
  5. temperatureto reflux with an oil bath
  6. customThe oil bath was removed
  7. addition100 milliliters of toluene and 20 milliliters of water were then added with efficient stirring
  8. customThe resulting two phase mixture was transferred into a separatory funnel
  9. customthe layers separated
  10. washThe organic phase was washed with water
  11. additiontreated under argon with 25 grams of alumina
  12. filtrationAfter the alumina was filtered off
  13. customthe organic phase was evaporated
  14. customto remove the toluene
  15. customThe above product compound was obtained by recrystallization of the residue from cyclohexane

Sources & evidence

ORD record
ord-aaa63ac14ab5427aadc9a48fd9b96cb4
Source dataset
uspto-grants-1998_05
Patent number
US05747205

Reaction notes

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