반응 #1004984

반응 방정식

9,10-Bis(3-methylanilino)phenanthrene

m-iodotoluene

potassium hydroxide

terpinolene

→

N,N,N′,N′-Tetra(3-methylphenyl)-9,10-diaminophenanthrene

용매

methanol tetrahydrofuran

반응 조건

후처리

1. 1
   기타This mixture was reacted at 115-125° C. for 2 hours in a nitrogen stream
2. 2
   기타After the reaction
3. 3
   workup.DISTILLATIONthe reaction solvent was distilled off by vacuum concentration
4. 4
   workup.ADDITIONTo the residue were added 5 mL of toluene, 67 mL of ethyl acetate, and 22 mL of water
5. 5
   기타The resultant mixture was subjected to liquid separation
6. 6
   workup.ADDITIONTo the organic layer was added 71 mL of methanol
7. 7
   온도The resultant solution was cooled for crystallization
8. 8
   기타Thus, the target compound (I-22) was obtained as light-yellow crude crystals
9. 9
   기타in an amount of 9.0 g (yield, 93.0%)
10. 10
    기타The target compound obtained

실험 절차

9,10-Bis(3-methylanilino)phenanthrene was mixed in an amount of 6.6 g (17.0 mmol) with 14.8 g (68.0 mmol) of m-iodotoluene, 3.82 g (68 mmol) of potassium hydroxide, 0.98 g (6.8 mmol) of copper-(I) bromide, 2.52 g (6.8 mmol) of ethyltriphenylphosphonium bromide, and 10 mL of terpinolene. This mixture was reacted at 115-125° C. for 2 hours in a nitrogen stream. After the reaction, the reaction solvent was distilled off by vacuum concentration. To the residue were added 5 mL of toluene, 67 mL of ethyl acetate, and 22 mL of water. The resultant mixture was subjected to liquid separation. To the organic layer was added 71 mL of methanol. The resultant solution was cooled for crystallization. Thus, the target compound (I-22) was obtained as light-yellow crude crystals in an amount of 9.0 g (yield, 93.0%). The target compound obtained had a melting point of 223-224° C. and a content as determined by HPLC of 99.6% (HPLC conditions: column, YMC-A-312; eluent, methanol/tetrahydrofuran (V/V=99/1); detection UV, 254 nm; flow rate, 1.0 mL/min).

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