Dimethylformamide → HCID 67312322, compound

HRID 2190417Notes

Reaction equation

HRID 2190417 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=O)(=[O:3])[CH3:2].CN(C)C=O.[F:19][C:20]([F:29])([F:28])[C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1.C(N(C(C)C)C(C)C)C>S(Cl)(Cl)=O.O>[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:7]([C:8]([NH:25][C:24]2[CH:26]=[CH:27][C:21]([C:20]([F:19])([F:28])[F:29])=[CH:22][CH:23]=2)=[O:10])[CH:6]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 99644-(Trifluoromethyl)anilineHCID 81531DiisopropylethylamineHCID 2386693-Acetoxybenzoic acid

Product 1

HCID 67312322HCID 67312322, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24386Thionyl ChlorideSolvent

Procedure

To a solution (20 mL) of 3-(acetyloxy)benzoic acid (18.0 g, 100 mmol) in thionyl chloride was added N,N-dimethylformamide (0.1 mL), and the mixture was stirred at room temperature for 1 hr. Excess reagents were evaporated under reduced pressure, and the obtained residue was dissolved in tetrahydrofuran (50 mL), and 4-(trifluoromethyl)aniline (24.2 g, 150 mmol) and N-ethyl-N-isopropylpropane-2-amine (19.4 g, 150 mmol) were successively added dropwise under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr, poured into water and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=5:1), and triturated with diethyl ether to give the title compound (27.7 g, 86%) as a pale-yellow solid.

Workup

  1. customExcess reagents were evaporated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in tetrahydrofuran (50 mL)
  3. temperaturecooling
  4. stirringThe reaction mixture was stirred at room temperature for 1 hr
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=5:1)
  9. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-5d3da83746044d47a3988fee4d0de61f
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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