Dicyclopentadiene → 4-(Cyclopent-2-en-1-yl)-6-methylbenzene-1,3-diamine

HRID 414784

Reaction equation

HRID 414784 reaction equation
[C:1]1([CH3:9])[C:2]([NH2:8])=[CH:3][C:4]([NH2:7])=[CH:5][CH:6]=1.C1C2C3C=CC(C2C=C1)C3.[CH3:20][CH2:21][CH2:22][CH2:23][CH3:24]>>[CH:22]1([C:5]2[CH:6]=[C:1]([CH3:9])[C:2]([NH2:8])=[CH:3][C:4]=2[NH2:7])[CH2:23][CH2:24][CH:20]=[CH:21]1

Participants

4

Reactant 3

HCID 6492DicyclopentadieneHCID 72612,4-DiaminotolueneHCID 8003Pentane

Product 1

HCID 140698844-(Cyclopent-2-en-1-yl)-6-methylbenzene-1,3-diamine

Conditions

Temperature
205 °C

Procedure

A 200 g (1.64 mol) portion of 2,4-toluenediamine, 162 g (1.23 mol, 2.45 equiv) of dicyclopentadiene, 200 g (2.78 mol) of pentane, and 20.0 g of an amorphous alumina-silica catalyst comprised of 13% alumina and 87% silica were charged to a 1000 cc pressure vessel equipped with a mechanical stirrer. The vessel was sealed and purged with nitrogen leaving a 32 psig nitrogen blanket. The vessel contents were heated to 205° C. with stirring and were maintained at that temperature for 22 hr. The contents were cooled to 150° C. and isolated catalyst free by hot filtration. Selective removal of residual hydrocarbons by vacuum distillation and analysis by gas chromatography (GC) revealed the following product mixture:

Workup

  1. additionwere charged to a 1000 cc pressure vessel
  2. customequipped with a mechanical stirrer
  3. customThe vessel was sealed
  4. custompurged with nitrogen leaving a 32 psig nitrogen blanket
  5. temperaturewere maintained at that temperature for 22 hr
  6. temperatureThe contents were cooled to 150° C.
  7. customisolated catalyst
  8. filtrationfree by hot filtration
  9. customremoval of residual hydrocarbons
  10. distillationby vacuum distillation and analysis by gas chromatography (GC)

Sources & evidence

ORD record
ord-8cb47ef8e4fb49899287132e68e527bd
Source dataset
uspto-grants-1988_12
Patent number
US04794194

Linked notes

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