Triethylamine → HCID 86658336, compound

HRID 2198026Notes

Reaction equation

HRID 2198026 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[NH2:6].C(N(CC)CC)C.Cl[CH2:24][CH2:25][N:26]=[C:27]=[O:28].C(OCC)(=O)C>C1(C)C=CC=CC=1>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]([N:6]2[CH2:24][CH2:25][NH:26][C:27]2=[O:28])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 160352-Chloroethyl isocyanate

Product 1

HCID 86658336HCID 86658336, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3,5-bis(trifluoromethyl)aniline (21.1 g) and triethylamine (13.9 mL) in toluene (200 ml) was slowly added 2-chloroethyl isocyanate (10.0 g) at 0° C., and the mixture was stirred at 60° C. for 4 hr. To the reaction solution was added ethyl acetate, and the mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (250 ml), sodium hydride (4.0 g) was slowly added at 0° C., and the mixture was stirred at room temperature for 3 hr. To the reaction solution was added ethyl acetate, and the mixture was washed with water and saturated brine, and dried over sodium sulfate. The solvent was concentrated under reduced pressure to give the title compound as a white solid (7.0 g, yield 26%).

Workup

  1. customat 0° C.
  2. washthe mixture was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in N,N-dimethylformamide (250 ml)
  6. additionsodium hydride (4.0 g) was slowly added at 0° C.
  7. stirringthe mixture was stirred at room temperature for 3 hr
  8. additionTo the reaction solution was added ethyl acetate
  9. washthe mixture was washed with water and saturated brine
  10. dry with materialdried over sodium sulfate
  11. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3df56dae543d4026b9b669a67288912a
Source dataset
uspto-grants-2012_12
Patent number
US08338622B2

Reaction notes

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