Dimethylformamide dimethyl acetal → HCID 53423662, compound

HRID 605586Notes

Reaction equation

HRID 605586 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:9](=[O:14])[C:10]([CH3:11])([CH3:13])[CH3:12])=[CH:17][N:18]([CH3:20])[CH3:19])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 101045691-(4-Chlorophenyl)-3,3-dimethylbutan-2-one

Product 1

HCID 53423662HCID 53423662, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
103 °C

Procedure

(b′) A 3 L, 4-necked, round-bottomed flask, equipped with a mechanical stirrer, digital thermometer, reflux condenser, and nitrogen inlet-outlet, is charged with 953 g (1.05 L) of a toluene solution containing 1-(4-chlorophenyl)-3,3-dimethyl-2-butanone and 173 g (200 mL) of toluene; then add by pump 232 g (259 mL) of N,N-dimethylformamide dimethyl acetal. The solution is heated to an internal temperature at 97-109° C. (reflux) and stirred at this temperature for 5 hours. One hundred (100) mL of solvent is distilled off over a period of 0.5 hours. After distillation is stopped, the mixture is heated to an internal temperature at 107-114° C. (reflux). The mixture is stirred at this temperature for an additional 1 hour. Three more distillations follow in a similar procedure. Then the reaction mixture is cooled to an internal temperature at 20-25° C. over 1 hour, and stirred at this temperature for 1 hour, filtered over a pad of 70 g of Celite and the pad was washed with 300 mL of toluene. Filtrates are combined and concentrated under vacuum (30-80 torr) at an internal temperature at 25-40° C. (maximum jacket temperature 50° C.) to collect about 800 g or 925 mL of solvent to afford 275 g of crude 2-(4-chlorophenyl)-1-(dimethylamino)-4,4-dimethyl-1-pentene-3-one (Theoretical yield: 173.6 g). This crude product is dissolved in 440 mL (380 g) of toluene and the removal of excess N,N-dimethylformamide dimethyl acetal is confirmed by 1H NMR. The solution can be held at 21-23° C. under nitrogen and then used in the next step.

Workup

  1. custom(b′) A 3 L, 4-necked, round-bottomed flask, equipped with a mechanical stirrer
  2. temperaturedigital thermometer, reflux condenser, and nitrogen inlet-outlet
  3. temperature(reflux)
  4. distillationOne hundred (100) mL of solvent is distilled off over a period of 0.5 hours
  5. distillationAfter distillation
  6. temperaturethe mixture is heated to an internal temperature at 107-114° C.
  7. temperature(reflux)
  8. stirringThe mixture is stirred at this temperature for an additional 1 hour
  9. temperatureThen the reaction mixture is cooled to an internal temperature at 20-25° C. over 1 hour
  10. stirringstirred at this temperature for 1 hour
  11. filtrationfiltered over a pad of 70 g of Celite
  12. washthe pad was washed with 300 mL of toluene
  13. concentrationconcentrated under vacuum (30-80 torr) at an internal temperature at 25-40° C. (maximum jacket temperature 50° C.)
  14. customto collect about 800 g or 925 mL of solvent

Sources & evidence

ORD record
ord-0ab82ed057c741abac1f698147a89def
Source dataset
uspto-grants-2011_03
Patent number
US07915264B2

Reaction notes

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