Acetone → HCID 18976935, compound

HRID 2393691Notes

Reaction equation

HRID 2393691 reaction equation
C[C:2]([CH3:4])=[O:3].P(Cl)(Cl)(Cl)=O.[CH3:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][N:20]1[C:32]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:26]2[C:21]1=[CH:22][CH:23]=C[CH:25]=2.[CH2:33]([O:35]C(=O)C)C>ClCCCl>[CH3:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][N:20]1[C:21]2[CH:22]=[CH:23][C:4]([CH:2]=[O:3])=[CH:25][C:26]=2[C:27]2[C:32]1=[CH:31][CH:30]=[C:29]([CH:33]=[O:35])[CH:28]=2

Participants

6

Reactant 4

HCID 180AcetoneHCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 18976934HCID 18976934, compound

Product 1

HCID 18976935HCID 18976935, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Under nitrogen atmosphere, 191 g (2.61 mol) of dimethylformaldehyde and 100 ml of 1,2-dichloroethane were put in a 1 L three-hole flask provided with an agitator, a thermometer, and a reflux condenser, and after cooling the mixture sufficiently to the temperature of 0° C., 197.6 g (1.29 mol) of phosphorous oxychloride was dropped down slowly thereto. The temperature of the reactant was raised to room temperature, and then the reactant was agitated for 1 hour, recooled to 0° C. and 21.0 g (0.067 mol) of N-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}carbazole diluted with 30 ml of 1,2-dichloroethane was added slowly thereto. After 1 hour, the reaction temperature was raised to 90° C. and the reaction was carried out for 24 hours. After reaction, the temperature was dropped to room temperature, and the reactant was diluted with 1.5 L of ice water, and then was extracted three times with 200 ml of dichloromethane. The extracted organic solutions were combined, and then washed consecutively with water, saturated NaHCO3 aqueous solution, and salt water. The resultant solution was dried with anhydrous magnesium sulfate, and after filtering and evaporating the solvent, a yellow viscous liquid was obtained. Such liquid was recrystallized three times with a small amount of ethylacetate, and 11.1 g (yield: 45%) of a light yellow solid having the melting point of 108° C. to 109° C. was obtained. [1H-NMR (CDCl3), δ 3.48-3.56(m, 11H, OCH2 and OCH3), 3.98(t, 2H, OCH2), 4.61(t, 2H, NCH2), 7.62(d, 2H, aromatic), 8.13(d, 2H, aromatic), 8.68(s, 2H, aromatic), 10.15(s, 2H, CHO)].

Workup

  1. customprovided with an agitator
  2. additionwas dropped down slowly
  3. customrecooled to 0° C.
  4. additionwas added slowly
  5. waitAfter 1 hour
  6. temperaturethe reaction temperature was raised to 90° C.
  7. waitthe reaction was carried out for 24 hours
  8. customAfter reaction
  9. additionthe temperature was dropped to room temperature
  10. extractionwas extracted three times with 200 ml of dichloromethane
  11. washwashed consecutively with water, saturated NaHCO3 aqueous solution, and salt water
  12. dry with materialThe resultant solution was dried with anhydrous magnesium sulfate
  13. filtrationafter filtering
  14. customevaporating the solvent
  15. customa yellow viscous liquid was obtained

Sources & evidence

ORD record
ord-b8834024b8c44641bada45dc1b517522
Source dataset
uspto-grants-1998_09
Patent number
US05807974

Reaction notes

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