Pyridine → HCID 69306580, compound

HRID 2055748Notes

Reaction equation

HRID 2055748 reaction equation
CN(C=O)C.S(Cl)([Cl:8])=O.N1C=CC=CC=1.[CH2:16]([O:25][C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:33]=1)[CH2:29]O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>ClCCl>[CH2:16]([O:25][C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:33]=1)[CH2:29][Cl:8])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 69305970HCID 69305970, compound

Product 1

HCID 69306580HCID 69306580, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1 L RBF was prepared containing 5 mL dry dichloromethane, a stir bar, a septum, an out-vent line and a nitrogen gas line. DMF (3.3 ml, 40.3 mmol) was added and the reaction mixture was cooled in an ice bath. Thionyl chloride (2.7 ml, 40.3 mmol) was added and the reaction mixture was stirred for 10 minutes. The ice bath was then removed and the reaction mixture was allowed to stir for an additional 10 minutes. The RBF was placed in an ice bath and a mixture of pyridine (2.72 ml, 33.6 mmol) and 3,5-dinonoxybenzylalcohol (13.2 g, 33.6 mmol) were added and dissolved in about 50 mL dichloromethane, drop-wise through the septum. After 15 minutes, the RBF was removed from the ice bath and the reaction was stirred for 2 hours after which the reaction mixture was placed in the refrigerator overnight. The solvent was removed by rotary evaporation. To the remaining organic matter, 100 mL of 50% ether/hexanes was added to dissolve the desired compound. A solid orange precipitate formed, the remaining liquid was decanted off and the precipitate was washed with an additional 100 mL of 50% ether/hexanes. The combined organic layers were vacuum filtered through a silica gel into a RBF and the solvent was removed under reduced pressure. The trace solvent was removed by high vacuum overnight. There was a 10.0 g yield or a 72.2% yield of the derivative. The NMR characterization data for this derivative is as follows. 1H NMR (300 MHz, CDCl3): 0.88 (t, J=6.3, 6H, CH2CH3), 1.1-1.55 (m, 28H, CH2(CH2)6), 1.76 (p, J=6.6, 4H, OCH2CH2), 3.93 (t, J=6.6, 4H,), 4.50 (d, J=5.8, 2H, CH2Cl), 6.39 (t, J=2.2, 1H, ArH), 6.51 (d, J=2.2, 2H, ArH).

Workup

  1. customA 1 L RBF was prepared
  2. temperaturethe reaction mixture was cooled in an ice bath
  3. customThe ice bath was then removed
  4. stirringto stir for an additional 10 minutes
  5. customThe RBF was placed in an ice bath
  6. additionwere added
  7. waitAfter 15 minutes
  8. customthe RBF was removed from the ice bath
  9. stirringthe reaction was stirred for 2 hours after which the reaction mixture
  10. customwas placed in the refrigerator overnight
  11. customThe solvent was removed by rotary evaporation
  12. additionTo the remaining organic matter, 100 mL of 50% ether/hexanes was added
  13. dissolutionto dissolve the desired compound
  14. customA solid orange precipitate formed
  15. customthe remaining liquid was decanted off
  16. washthe precipitate was washed with an additional 100 mL of 50% ether/hexanes
  17. filtrationfiltered through a silica gel into a RBF
  18. customthe solvent was removed under reduced pressure
  19. customThe trace solvent was removed by high vacuum overnight
  20. customyield

Sources & evidence

ORD record
ord-f3c296e23c1d4e70bc5b1b1f371814b2
Source dataset
uspto-grants-2008_02
Patent number
US07332529B2

Reaction notes

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