Sulfuric Acid → HCID 18381175, compound

HRID 2297357Notes

Reaction equation

HRID 2297357 reaction equation
S(=O)(=O)(O)O.Br[C:7]1[CH:24]=[CH:23][C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH:8]=1.[C:25]1([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].O>[C:32]1([N:31]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:7]2[CH:24]=[CH:23][C:22]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9]=3[CH:8]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 11487DiphenylamineHCID 183811742-Bromotriphenylene

Product 1

HCID 18381175HCID 18381175, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Triphenylene and N-bromosuccinimide were introduced to mixture (4:1) of water and sulfuric acid and stirred for five hours at 60° C. The object compound was extracted from the reacted solution using toluene and neutralized with 5% sodium hydrogencarbonate solution. After drying the compound by using magnesium sulfate, coarse crystals of the compound, left after evaporation of the solvent, were recrystallized from the toluene-hexane mixed solvent, to prepare 2-bromotriphenylene compound. Thereafter, the 2-bromotriphenylene compound, diphenylamine, potassium carbonate and copper powder were introduced in a three-necked flask, and stirred for 30 hours at 200° C. The reaction product was subjected to extraction using toluene and to washing using water. Then, the product was subjected to drying using magnesium sulfate, evaporation of the solvent, and separation refinement by silica gel column chromatography using a 1:2 mixture of toluene and hexane to obtain 2-diphenylaminotriphenylene.

Workup

  1. extractionThe object compound was extracted from the reacted solution
  2. customAfter drying the compound
  3. waitcoarse crystals of the compound, left
  4. customafter evaporation of the solvent
  5. customwere recrystallized from the toluene-hexane mixed solvent
  6. customto prepare 2-bromotriphenylene compound
  7. stirringstirred for 30 hours at 200° C
  8. extractionThe reaction product was subjected to extraction
  9. washto washing
  10. customto drying
  11. custommagnesium sulfate, evaporation of the solvent, and separation refinement by silica gel column chromatography
  12. additiona 1:2 mixture of toluene and hexane

Sources & evidence

ORD record
ord-98cd0f28b0924e3cb4be875ba1e449f5
Source dataset
uspto-grants-2002_12
Patent number
US06492041B2

Reaction notes

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