Methyl iodide → HCID 67329604, compound

HRID 925058Notes

Reaction equation

HRID 925058 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[C:11]([NH:19][P:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)([CH3:3])[CH3:2].[CH2:27]([Li])CCC.CI>C(OCC)C>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[C:11]([N:19]([P:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH3:27])[C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 67298216HCID 67298216, compoundHCID 178418339Butyllithium

Product 1

HCID 67329604HCID 67329604, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

N′-(2-isopropylphenyl)-N-(diisopropylphosphino)-4-methylbenzamidine (1.40 g, 3.0 mmol) was dissolved in 25 mL of diethylether and cooled to 0° C. Butyllithium (1.50 mL of 2.0 M solution in pentane, 3.0 mmol) was added dropwise, producing a cloudy yellow suspension. The slurry was warmed to room temperature and stirred for 2 hours. Methyliodide (1.5 mL of 2.0 M solution in THF) was added dropwise at room temperature and stirred continued for 1 hour. The solution became clear yellow. The solvent was removed under vacuum and replaced with 20 mL of diethylether. A small amount of solid (presumably LiI) was removed by filtration and the filtrate was taken to dryness, yielding 0.94 g (65%) of sticky yellow solid.

Workup

  1. customproducing a cloudy yellow suspension
  2. temperatureThe slurry was warmed to room temperature
  3. stirringstirred
  4. waitcontinued for 1 hour
  5. customThe solvent was removed under vacuum
  6. customA small amount of solid (presumably LiI) was removed by filtration

Sources & evidence

ORD record
ord-efe619c8b86d4c8ea60cf11655c490ae
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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