O-Phenylenediamine → HCID 18003188, compound

HRID 274097Notes

Reaction equation

HRID 274097 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].Cl[C:10]1(Cl)[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2>>[NH2:7][C:2]1[CH:3]=[C:4]([C:10]2([C:5]3[CH:4]=[CH:3][C:2]([NH2:7])=[C:1]([NH2:8])[CH:6]=3)[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:5]=[CH:6][C:1]=1[NH2:8]

Participants

3

Reactant 2

HCID 7243O-Phenylenediamine2×HCID 906899,9-Dichloro-9H-fluorene

Product 1

HCID 18003188HCID 18003188, compound

Conditions

Temperature
105 °C

Procedure

Into a three-necked 100 mL round-bottomed flask is placed o-phenylene diamine (26 g). The flask is then equipped with a drying tube, magnetic stirbar, thermometer, powder addition funnel, and nitrogen inlet. The o-phenylene diamine is then stirred and heated to 105° C. and solid 9,9-dichlorofluorene is added to the melt. An immediate reaction occur s as evidenced by a color change to dark brown, formation of a copious precipitate and an increase in temperature to 110°-120° C. The temperature is then increased to 130° C. and held there for 4 hours during which time the mixture becomes more liquid. The reaction is then allowed to cool and the excess o-phenylenediamine is removed by pouring the reaction mixture into ethanol and filtering. The resulting dark brown solid is recrystallized from toluene to yield 9,9-bis(3,4-diaminophenyl)fluorene. HNMR (DMSO): delta 4.97 (bs, 8H, NH2), 6.07-6.11 (m, 2H), 6.31-6.42 (m, 4H), 7.17-7.33 (m, 6H), 7.76-7.79 (m, 2H). C-13 NMR (DMSO) (ppm): 152.55, 139.7 1,136.29, 134.37, 132.64, 127.56, 127.17, 126.40, 120.37, 118.36, 117.69, 115.63, 115.11, 64.4 (quaternary carbon) where s=singlet, m=multiplet, and bs=broad singlet.

Workup

  1. customInto a three-necked 100 mL round-bottomed flask is placed
  2. customThe flask is then equipped with a drying tube
  3. additionmagnetic stirbar, thermometer, powder addition funnel, and nitrogen inlet
  4. customAn immediate reaction
  5. temperaturean increase in temperature to 110°-120° C
  6. temperatureThe temperature is then increased to 130° C.
  7. temperatureto cool
  8. customthe excess o-phenylenediamine is removed
  9. additionby pouring the reaction mixture into ethanol
  10. filtrationfiltering
  11. customThe resulting dark brown solid is recrystallized from toluene

Sources & evidence

ORD record
ord-5fea3452fc034381be8c548992bc5f80
Source dataset
uspto-grants-1995_02
Patent number
US05387725

Reaction notes

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