Chlorodiisopropylphosphine → HCID 68274899, compound

HRID 925057Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]=[C:12]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([CH3:30])([CH3:29])[CH3:28])[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.Cl[P:37]([CH:41]([CH3:43])[CH3:42])[CH:38]([CH3:40])[CH3:39]>C(OCC)C>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]=[C:12]([N:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([CH3:30])([CH3:29])[CH3:28])[P:37]([CH:41]([CH3:43])[CH3:42])[CH:38]([CH3:40])[CH3:39])[C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

N′-(2-tert-butylphenyl)-N-(2-tert-butylphenyl)-4-methylbenzamidine (NS Amidine II) (1.20 g, 3.0 mmol) was dissolved in 50 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 light yellow solution. The solution was warmed to room temperature and stirred for 2 hours. Chlorodiisopropylphosphine (0.48 mL, 3.0 mmol) was added slowly at room temperature. A white suspension formed, which was stirred overnight at room temperature. The slurry was filtered to remove a small amount of white solid, presumably lithium chloride, and the solvent was removed in vacuo to produce 1.35 g (87%) of yellow solid.

Workup

customproducing a light yellow solution
temperatureThe solution was warmed to room temperature
customA white suspension formed
stirringwhich was stirred overnight at room temperature
filtrationThe slurry was filtered
customto remove a small amount of white solid, presumably lithium chloride
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-c5374b2846ce49018524adf0c0003c08
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09283555B2

Reaction notes

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