N,N-Dimethylaniline → HCID 73947316, compound

HRID 1893479Notes

Reaction equation

HRID 1893479 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=O)[C:8]3[N:9]2[CH:12]=[CH:13][N:14]=3)=[CH:4][C:3]=1[C:16]([F:19])([F:18])[F:17].CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:31])=O>O.[OH-].[Na+]>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([Cl:31])[C:8]3[N:9]2[CH:12]=[CH:13][N:14]=3)=[CH:4][C:3]=1[C:16]([F:19])([F:18])[F:17]

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 68666114HCID 68666114, compound

Product 1

HCID 73947316HCID 73947316, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
120 °C

Procedure

8-Bromo-7-(trifluoromethyl)imidazo[1,2-a]quinoxalin-4(5H)-one (9.4 g, 0.0283 mol) is stirred under nitrogen with N,N-dimethylaniline (14.5 mL, 0.1123 mol) and phosphoryl chloride (190 mL, 2.0119 mol) at reflux (120° C.) for 1.5 hour. After cooling down to room temperature, the mixture is slowly poured in a mixture of water (2 L) and sodium hydroxide 5N (1 L) below 10° C. The mixture is extracted four times with ethyl acetate (200 mL) and the combined organic phases are washed with water (200 mL), dried over sodium sulfate and concentrated to about 100 mL. Cyclohexane (500 mL) is added at room temperature. The mixture is cooled to 0-5° C. and filtered. The cake is washed with cyclohexane and dried under vacuum to afford the title compound as a yellow solid (7.98 g, 80.4%)

Workup

  1. temperatureAfter cooling down to room temperature
  2. extractionThe mixture is extracted four times with ethyl acetate (200 mL)
  3. washthe combined organic phases are washed with water (200 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to about 100 mL
  6. additionCyclohexane (500 mL) is added at room temperature
  7. temperatureThe mixture is cooled to 0-5° C.
  8. filtrationfiltered
  9. washThe cake is washed with cyclohexane
  10. customdried under vacuum

Sources & evidence

ORD record
ord-1528f5aa9a924764b25fdaae60c49e56
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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