Phosphine → HCID 178425658, compound

HRID 925047Notes

Reaction equation

[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[C:11]([NH2:19])[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)([CH3:3])[CH3:2].C([Li])CCC.Cl[P:26]([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28].P>C(OCC)C>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[N:19][P:26]([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])[C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

N2-(2-isopropylphenyl)-4-methylbenzamidine (1.26 g, 5.0 mmol) was dissolved in 25 mL of diethylether and cooled to 0° C. Butyllithium (2.50 mL of 2.0 M solution in pentane, 5.0 mmol) was added dropwise, producing a fluffy white suspended solid. The slurry was warmed to room temperature and stirred for 2 hours. Chlorodiisopropylphosphine (0.80 mL, 5.0 mmol) was added slowly at room temperature. The suspended solid became finer and denser and the solution became slightly yellow upon complete addition of the phosphine. Stirring was continued for 1 hour. The solution was filtered to remove a small amount of white solid, presumably lithium chloride, and the solvent was removed in vacuo. The yellow foamy residue was suspended in 25 mL of pentane, stirred for 2 hours and taken to dryness under vacuum, affording 1.64 g (70%) of yellow solid.

Workup

customproducing a fluffy
temperatureThe slurry was warmed to room temperature
stirringStirring
waitwas continued for 1 hour
filtrationThe solution was filtered
customto remove a small amount of white solid, presumably lithium chloride
customthe solvent was removed in vacuo
stirringstirred for 2 hours

Sources & evidence

ORD record: ord-dd1b1856589b4c3bbda201c64247be74
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09283555B2

Reaction notes

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