Toluene → HCID 57887405, compound

HRID 888707Notes

Reaction equation

HRID 888707 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[C:6]1([CH3:12])[CH:11]=[CH:10]C=C[CH:7]=1.C1CC=CC=1.[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19]>O.C(OCC)(=O)C>[C:18]([NH:22][C:1]([CH:2]1[CH2:12][CH:6]2[CH2:7][CH:3]1[CH:10]=[CH:11]2)=[O:4])([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 1140Toluene2×HCID 6385Tert-ButylamineHCID 7612CyclopentadieneHCID 13140Acryloyl chloride

Product 1

HCID 57887405HCID 57887405, compoundYield 26.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A 2 L three-necked flask fitted with a thermometer, a stirrer, a nitrogen inlet tube and a dropping funnel was charged with 217.2 g (2.400 mol) of acryloyl chloride and 520 g of toluene, and the internal temperature was cooled to 0° C. 190.4 g (2.880 mol) of cyclopentadiene was then added dropwise from the dropping funnel over a period of 1 hour. Following completion of the dropwise addition, the resulting mixture was stirred for 1 hour at 0° C., thereby preparing a reaction intermediate solution. A 2 L three-necked flask fitted with a thermometer, a stirrer, a nitrogen inlet tube and a dropping funnel was charged with 201.1 g (2.750 mol) of tert-butylamine and 513 g of toluene, and the internal temperature was cooled to 0° C. The reaction intermediate solution prepared previously was added dropwise thereto from the dropping funnel over a period of 1.5 hours, and the internal temperature was then raised to 25° C. To the reaction mixture were added 1.800 ml of ethyl acetate and 300 ml of water, and following 30 minutes of stirring, the resulting mixture was allowed to stand to obtain an organic layer. The resulting organic layer was concentrated under reduced pressure. To the obtained concentrate were added 750 ml of ethyl acetate and 250 ml of hexane, and the resulting mixture was heated to 40° C. Following cooling of the resultant to 2° C. with stirring, the precipitated crystals were collected by filtration. The obtained crystals were dried under reduced pressure, thereby obtaining 124.3 g (0.643 mol; yield: 26.8%) of N-tert-butylbicyclo[2.2.1]hept-5-ene-2-carboxamide having the following physical properties.

Workup

  1. customA 2 L three-necked flask fitted with a thermometer, a stirrer, a nitrogen inlet tube and a dropping funnel
  2. additioncompletion of the dropwise addition
  3. custompreparing a reaction intermediate solution
  4. customA 2 L three-necked flask fitted with a thermometer, a stirrer, a nitrogen inlet tube and a dropping funnel
  5. temperaturethe internal temperature was cooled to 0° C
  6. customThe reaction intermediate solution prepared previously
  7. additionwas added dropwise
  8. waitfrom the dropping funnel over a period of 1.5 hours
  9. temperaturethe internal temperature was then raised to 25° C
  10. waitfollowing 30 minutes
  11. stirringof stirring
  12. customto obtain an organic layer
  13. concentrationThe resulting organic layer was concentrated under reduced pressure
  14. concentrationTo the obtained concentrate
  15. additionwere added 750 ml of ethyl acetate and 250 ml of hexane
  16. temperaturethe resulting mixture was heated to 40° C
  17. temperatureFollowing cooling of the resultant to 2° C.
  18. stirringwith stirring
  19. filtrationthe precipitated crystals were collected by filtration
  20. customThe obtained crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-2ebad205fb9941a1b0613df1c69faede
Source dataset
uspto-grants-2012_08
Patent number
US08252509B2

Reaction notes

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