Water → HCID 178425628, compound

HRID 925021Notes

Reaction equation

HRID 925021 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([CH3:3])[CH3:2].[CH2:11]([Li])CCC.NC1C=CC=CC=1.[C:23]1(C)[C:24]([C:29]#[N:30])=[CH:25][CH:26]=[CH:27][CH:28]=1.O>CCCCC.C(OCC)C>[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][C:29](=[NH:30])[C:24]1[CH:23]=[CH:28][C:27]([CH3:11])=[CH:26][CH:25]=1)([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 962WaterHCID 6115AnilineHCID 107212-MethylbenzonitrileHCID 125612-IsopropylanilineHCID 178418339Butyllithium

Product 1

HCID 178425628HCID 178425628, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Conditions

Temperature
0 °C

Procedure

2-isopropylaniline (5.0 mL, 36.1 mmol) was added to 100 mL of diethylether and cooled to 0° C. Butyllithium (18.0 mL of 2.0 M solution in pentane, 36.1 mmol) was added dropwise to the cooled aniline solution, affording a light yellow suspension after complete addition. The slurry was warmed to room temperature and stirred for 2 hours. Toluonitrile (4.23 g, 36.1 mmol) was added slowly resulting in the formation of a bright yellow solution 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-brown 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 50 mL of pentane and stirred for 2 hours. Filtration of the slurry yielded 7.56 g (83%) of light yellow solid. 1H NMR (400 MHz, CDCl3): 7.77 (d, 2H), 7.30 (d, 1H), 7.22 (d, 2H), 7.15 (t, 1H), 7.04 (t, 1H), 6.83 (d, 1 H), 4.70 (s, 2H), 3.16 (septet, 1H), 2.40 (s, 3H), 1.19 (d, 6H).

Workup

  1. customaffording a light yellow suspension
  2. additionafter complete addition
  3. temperatureThe slurry was warmed to room temperature
  4. customresulting in the formation of a bright yellow solution
  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-brown 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
  18. customyielded 7.56 g (83%) of light yellow solid

Sources & evidence

ORD record
ord-7e04aea1866b434fb9ecae49dd49ab79
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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