N,N-Dimethylaniline → HCID 20463605, compound

HRID 325995Notes

Reaction equation

HRID 325995 reaction equation
[CH2:1]([N:3]([CH2:23][CH3:24])[C:4]1[CH:5]=[C:6]([CH:10]2[C:19]3[C:14](=[CH:15][C:16]([N:20]([CH3:22])[CH3:21])=[CH:17][CH:18]=3)[C:12](=[O:13])[O:11]2)[CH:7]=[CH:8][CH:9]=1)[CH3:2].[CH3:25][N:26]([CH3:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[Cl-].[Al+3].[Cl-].[Cl-].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+]>ClCC(Cl)(Cl)Cl.[OH-].[Na+]>[CH2:23]([N:3]([CH2:1][CH3:2])[C:4]1[CH:5]=[C:6]([C:10]2([C:30]3[CH:31]=[CH:32][C:27]([N:26]([CH3:33])[CH3:25])=[CH:28][CH:29]=3)[C:19]3[C:14](=[CH:15][C:16]([N:20]([CH3:22])[CH3:21])=[CH:17][CH:18]=3)[C:12](=[O:13])[O:11]2)[CH:7]=[CH:8][CH:9]=1)[CH3:24]

Participants

7

Reactant 4

HCID 949N,N-DimethylanilineHCID 24412Potassium PersulfateHCID 6451240Aluminum(III) Chloride2×HCID 204635863-[3-(Diethylamino)phenyl]-6-(dimethylamino)-2-benzofuran-1(3H)-one

Product 1

HCID 20463605HCID 20463605, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 124181,1,1,2-TetrachloroethaneSolvent2×HCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
50 °C

Procedure

33 g of 3-(m-diethylaminophenyl)-6-dimethylaminophthalide and 13 g of dimethylaniline were dissolved in 300 cc of tetrachloroethane. 14 g of anhydrous aluminum chloride was added to the solution, and then the mixture was heated at 50° C. for 3 hours with stirring. After the termination of reaction, 30% aqueous solution of caustic soda was added to the mixture to dissolve aluminum chloride while cooling with ice. Tetrachloroethane phase was steam distilled to remove unreacted dimethylaniline and tetrachloroethane. The remaining aqueous phase was neutralized with acetic acid to obtain a white solid. This solid was dissolved in 600 cc of 2.5% aqueous solution of caustic soda, and then heated at 50° C. 600 cc of 5% aqueous solution of potassium persulfate was added dropwise to the above solution, and then the mixture was heated at 60° C. for 3 hours. After the termination of reaction, the resultant precipitates were filtered and recrystallized from methanol to obtain 31 g of 3-(m-diethylaminophenyl)-3-(p-dimethylaminophenyl)- 6-dimethylaminophthalide having the following structure whose m.p. was 177°-178° C. in the form of colourless crystals. This compound become green on contact with silica gel. ##STR73##

Workup

  1. additionwas added to the mixture
  2. temperaturewhile cooling with ice
  3. distillationdistilled
  4. customto remove unreacted dimethylaniline and tetrachloroethane
  5. customto obtain a white solid
  6. temperatureheated at 50° C
  7. temperaturethe mixture was heated at 60° C. for 3 hours
  8. customAfter the termination of reaction
  9. customthe resultant precipitates
  10. filtrationwere filtered
  11. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5596f32aa8294451a2e5fe5e4c016c79
Source dataset
uspto-grants-1984_04
Patent number
US04443614

Reaction notes

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