2,6-Lutidine → HCID 21113542, compound

HRID 1767266Notes

Reaction equation

HRID 1767266 reaction equation
[S:1](=[O:4])(=O)=[O:2].N1C(C)=CC=CC=1C.[CH2:13]([NH:16][CH2:17][CH2:18][C:19]#[N:20])[CH:14]=[CH2:15].P(Cl)(Cl)([Cl:23])=O>ClCCCl>[CH2:13]([N:16]([CH2:17][CH2:18][C:19]#[N:20])[S:1]([Cl:23])(=[O:4])=[O:2])[CH:14]=[CH2:15]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 24682Sulfur trioxideHCID 24813Phosphorus oxychlorideHCID 2373603-(prop-2-en-1-ylamino)propanenitrile

Product 1

HCID 21113542HCID 21113542, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
22 °C

Procedure

64.8 g (0.641 mol) of sulfur trioxide were added as a 57% solution in 1,2-dichloroethane at from 0 to 5° C. with stirring within 15 minutes to a solution of 90.6 g (0.846 mol) of 2,6-lutidine in 200 ml of 1,2-dichloroethane, followed by washing with 40 ml of 1,2-dichloroethane and stirring for 15 minutes until the temperature had risen to 22° C. Subsequently, 42.4 g (0.385 mol) of N-allyl-N-(2-cyanoethyl)amine were added at from 20 to 30° C. with stirring within 15 minutes, followed by washing with 40 ml of 1,2-dichloroethane and stirring at 50° C. for 15 minutes. After cooling to 22° C., 70.8 g (0.61 mol) of phosphorus oxychloride were added with stirring at from 20 to 30° C. within 15 minutes, followed by washing with 120 ml of 1,2-dichloroethane and heating to 70° C. After stirring at this temperature for 1 hour, the reaction mixture was allowed to cool to 25° C., concentrated under reduced pressure and distilled through a Normag column head with a 10 cm column. 32.3 g (40% of theory) of the title compound with a b.p. of from 110 to 116° C./0.4 mbar were obtained. Refractive index: nD23=1.4948.

Workup

  1. washby washing with 40 ml of 1,2-dichloroethane
  2. customhad risen to 22° C
  3. stirringwith stirring within 15 minutes
  4. washby washing with 40 ml of 1,2-dichloroethane
  5. stirringstirring at 50° C. for 15 minutes
  6. stirringwith stirring at from 20 to 30° C. within 15 minutes
  7. washby washing with 120 ml of 1,2-dichloroethane
  8. temperatureheating to 70° C
  9. stirringAfter stirring at this temperature for 1 hour
  10. temperatureto cool to 25° C.
  11. concentrationconcentrated under reduced pressure
  12. distillationdistilled through a Normag column head with a 10 cm column
  13. customof from 110 to 116° C./0.4 mbar were obtained

Sources & evidence

ORD record
ord-22a0e0aea60a4152ade9067fa6b338ad
Source dataset
uspto-grants-2007_06
Patent number
US07232926B2

Reaction notes

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