1,10-Phenanthroline → HCID 16150869, compound

HRID 1288675Notes

Reaction equation

HRID 1288675 reaction equation
[C:1]1([N:7]([C:21]2[CH:22]=[C:23]([CH3:27])[CH:24]=[CH:25][CH:26]=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:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([N:41]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:42]3[CH:43]=[C:44]([CH3:48])[CH:45]=[CH:46][CH:47]=3)=[CH:37][CH:36]=2)=[CH:31][CH:30]=1.N1[C:68]2[C:59](=[CH:60][CH:61]=[C:62]3[C:67]=2[N:66]=[CH:65][CH:64]=[CH:63]3)[CH:58]=CC=1.[OH-].[K+]>C1(C)C(C)=CC=CC=1>[C:1]1([N:7]([C:21]2[CH:22]=[C:23]([CH3:27])[CH:24]=[CH:25][CH:26]=2)[C:8]2[CH:9]=[CH:10][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:66]([C:67]6[CH:68]=[C:59]([CH3:58])[CH:60]=[CH:61][CH:62]=6)[C:65]6[CH:64]=[CH:63][CH:6]=[CH:1][CH:2]=6)=[CH:9][CH:10]=5)=[CH:15][CH:16]=4)[C:29]4[CH:34]=[CH:33][C:32]([C:35]5[CH:40]=[CH:39][C:38]([N:41]([C:42]6[CH:43]=[C:44]([CH3:48])[CH:45]=[CH:46][CH:47]=6)[C:49]6[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=6)=[CH:37][CH:36]=5)=[CH:31][CH:30]=4)=[CH:16][CH:15]=3)=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 13181,10-PhenanthrolineHCID 14797Potassium HydroxideHCID 107188194'-Iodo-N-(3-methylphenyl)-N-phenyl[1,1'-biphenyl]-4-amineHCID 10904254HCID 10904254, compound

Product 1

HCID 16150869HCID 16150869, 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-phenyl-N-m-tolyl benzidine (8.0 grams, 0.023 mol), 4'-iodo-N-phenyl-N-m-tolyl-4-aminobiphenyl (17.5 grams, 0.038 mol), xylene (15 milliliters), 1,10-phenanthroline (0.34 gram, 1.9 mmol), cuprous chloride (0.188 gram, 1.9 mmol), and potassium hydroxide flakes (17.06 grams, 0.3 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 25 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 most of the toluene. The above product, Compound (1), was obtained by recrystallization of the residue from cyclohexane. Yield: 12.3 grams; m.p. 234.28° C.; Tg 134° 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 25 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 most of the toluene

Sources & evidence

ORD record
ord-2c54fe9974914c2685b83a47d962fddc
Source dataset
uspto-grants-1998_05
Patent number
US05747205

Reaction notes

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