Dimethylamine → HCID 53791670, compound

HRID 1676222Notes

Reaction equation

HRID 1676222 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]([CH:9]=O)[CH3:8].[CH:11](=[O:16])[CH2:12][CH2:13][CH2:14][CH3:15].C([O-])([O-])=O.[K+].[K+].CNC>ClCCCl>[CH3:8][N:7]([CH:9]=[C:12]([CH2:13][CH2:14][CH3:15])[CH:11]=[O:16])[CH3:6]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 6228DimethylformamideHCID 8063PentanalHCID 11430Potassium Carbonate2×HCID 24813Phosphorus oxychloride

Product 1

HCID 53791670HCID 53791670, compoundYield 5.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of phosphorus oxychloride (2.330 mL, 25.00 mmol, Aldrich) in 1,2-dichloroethane (5.0 mL) at 0° C. was added DMF (7.74 mL, 100 mmol, EMD) in 1,2-dichloroethane (10.0 mL) during the course of 10 min. The mixture was stirred at 0° C. for 20 min and then warmed up to room temperature. After stirring at room temperature for 3 hrs, valeraldehyde (2.66 mL, 25.0 mmol, Aldrich) in 1,2-dichloroethane (5.0 mL) was added dropwise (5 min) and the resulting mixture was stirred at room temperature for 50 min and at 85° C. for 50 min. The cooled reaction mixture was poured into a mixture of ice and K2CO3 (7.5 g) followed by addition of saturated K2CO3 aqueous solution until the pH of the mixture was around 10. To the above mixture, dimethyl amine (8.0 mL, 40 wt. % solution in water, Aldrich) was added and the reaction mixture was heated at 80° C. for 1 hr, cooled and evaporated under reduced pressure to remove 1,2-dichloroethane. The resulting mixture was then heated at 95° C. for 1 hr, cooled to room temperature and extracted with EtOAc (3×). The combined extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was distilled under reduced pressure (1 torr at 145-155° C. of oil bath) to yield the title compound (200 mg, 5.7%) as an orange oil. 1H NMR (500 MHz, CDCl3) δ 8.85 (s, 1H), 6.48 (s, 1H), 3.13 (s, 6H), 2.30-2.45 (m, 2H), 1.32-1.53 (m, 2H), 0.93 (t, J=7.42 Hz, 3H).

Workup

  1. temperaturewarmed up to room temperature
  2. stirringAfter stirring at room temperature for 3 hrs
  3. stirringthe resulting mixture was stirred at room temperature for 50 min and at 85° C. for 50 min
  4. customThe cooled reaction mixture
  5. temperaturethe reaction mixture was heated at 80° C. for 1 hr
  6. temperaturecooled
  7. customevaporated under reduced pressure
  8. customto remove 1,2-dichloroethane
  9. temperatureThe resulting mixture was then heated at 95° C. for 1 hr
  10. temperaturecooled to room temperature
  11. extractionextracted with EtOAc (3×)
  12. washThe combined extracts were washed with brine
  13. dry with materialdried (Na2SO4)
  14. concentrationconcentrated in vacuo
  15. distillationThe residue was distilled under reduced pressure (1 torr at 145-155° C. of oil bath)

Sources & evidence

ORD record
ord-2d65f8a6e5774e5bba1214a48a95fe00
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

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