Chlorodiisopropylphosphine → N1-(2-isopropyl-6-methylphenyl)-N2-(diisopropyl-phosphino)-4-methylbenzamidine

HRID 925039Notes

Reaction equation

HRID 925039 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[NH:11][C:12](=[NH:20])[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)([CH3:3])[CH3:2].C([Li])CCC.Cl[P:27]([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29]>>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[NH:11][C:12](=[N:20][P:27]([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 538967ChlorodiisopropylphosphineHCID 178418339ButyllithiumHCID 178425631HCID 178425631, compound

Product 1

HCID 178425661N1-(2-isopropyl-6-methylphenyl)-N2-(diisopropyl-phosphino)-4-methylbenzamidine

Procedure

Procedure as described for NP Amidine I using the following amounts: 1.33 g of N1-(2-isopropyl-6-methylphenyl)-4-methylbenzamidine (Amidine V, 5.0 mmol), 2.50 mL of 2.0 M butyllithium (5.0 mmol), 0.80 mL chlorodiisopropylphosphine (5.0 mmol). After filtration to remove lithium chloride and removal of solvent, a yellow semi-solid was isolated (1.86 g, 97%).

Workup

  1. filtrationAfter filtration
  2. customto remove
  3. customlithium chloride and removal of solvent
  4. customa yellow semi-solid was isolated (1.86 g, 97%)

Sources & evidence

ORD record
ord-0dc94fc71bc24b18b415f2c8fc3d938c
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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