N,N-Dimethylaniline → HCID 25184970, compound

HRID 1878096Notes

Reaction equation

HRID 1878096 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[N:17]=[C:16](O)[CH:15]=[C:14]([C:19]([F:22])([F:21])[F:20])[N:13]=2)=[CH:10][CH:11]=1)=[O:4].CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:34]>C(#N)C.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[N:17]=[C:16]([Cl:34])[CH:15]=[C:14]([C:19]([F:22])([F:21])[F:20])[N:13]=2)=[CH:10][CH:11]=1)=[O:4]

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178520804HCID 178520804, compound

Product 1

HCID 25184970HCID 25184970, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of compound of example 53 (0.100 g, 0.301 mmol) in acetonitrile (5 mL), was added benzyl triethyl ammonium chloride (0.274 g, 1.204 mmol), dimethylaniline (0.143 g, 1.183 mmol) and POCl3 (2.3 g, 15.05 mmol). The reaction mixture was refluxed for 3 hours. Acetonitrile was removed under vacuum, reaction mass neutralized by sodium bicarbonate solution and extracted with ethyl acetate (3×20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain the crude product, which was purified by column chromatography (silica gel, 5 % methanol in chloroform as an eluent) to obtain the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customAcetonitrile was removed under vacuum, reaction mass
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto obtain the crude product, which
  7. customwas purified by column chromatography (silica gel, 5 % methanol in chloroform as an eluent)

Sources & evidence

ORD record
ord-ae62c458ed7a44dfa822856df8b7bfd8
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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