Water → HCID 178424804, compound

HRID 925012Notes

Reaction equation

HRID 925012 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C([Li])CCC.NC1C=CC=CC=1.[C:22](#[N:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CCCCC.C(OCC)C>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][C:22](=[NH:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 5

HCID 962WaterHCID 6115AnilineHCID 68962,6-DimethylanilineHCID 7505BenzonitrileHCID 178418339Butyllithium

Product 1

HCID 178424804HCID 178424804, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Conditions

Temperature
0 °C

Procedure

2,6-dimethylaniline (6.15 mL, 50.0 mmol) was added to 100 mL of diethylether and cooled to 0° C. Butyllithium (26.0 mL of 2.0 M solution in diethylether, 52.0 mmol) was added dropwise to the cooled aniline solution, affording an off-white solid after complete addition. The slurry was warmed to room temperature and stirred for 2 hours. Benzonitrile (5.2 mL, 51.0 mmol) was added slowly resulting in the formation of a suspended yellow-orange solid after complete addition. Stirring was continued for 1 hour and the solvent was removed in vacuo. Tetrahydrofuran (150 mL) was added and the mixture was refluxed overnight under argon, yielding a dark orange-red solution. Distilled water (2.0 mL, 112 mmol) was added and the mixture became a milky yellow solution after stirring for 30 minutes at room temperature. Solid, presumably lithium hydroxide, was removed via aerobic filtration and the remaining solvent was removed in vacuo, to produce a light yellow solid. The solid was slurried in 80 mL of pentane and stirred for 2 hours. Filtration of the slurry yielded 10.28 g (92%) of white solid. 1H NMR (400 MHz, CDCl3): 7.93 (d, 2H), 7.48 (m, 3H), 7.06 (d, 2H), 6.90 (t, 1 H), 4.58 (s, 2H), 2.17 (s, 6H).

Workup

  1. customaffording an off-white solid
  2. additionafter complete addition
  3. temperatureThe slurry was warmed to room temperature
  4. customresulting in the formation of a suspended yellow-orange solid
  5. additionafter complete addition
  6. stirringStirring
  7. waitwas continued for 1 hour
  8. customthe solvent was removed in vacuo
  9. additionTetrahydrofuran (150 mL) was added
  10. temperaturethe mixture was refluxed overnight under argon
  11. customyielding a dark orange-red solution
  12. stirringafter stirring for 30 minutes at room temperature
  13. customSolid, presumably lithium hydroxide, was removed via aerobic filtration
  14. customthe remaining solvent was removed in vacuo
  15. customto produce a light yellow solid
  16. stirringstirred for 2 hours
  17. filtrationFiltration of the slurry

Sources & evidence

ORD record
ord-727e31fecb3948259da19dc89c9cf56f
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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