Methyl iodide → N'-(2-n-propylphenyl)-N-(diphenylphosphino)-N-methyl-4-methylbenzamidine

HRID 925059Notes

Reaction equation

HRID 925059 reaction equation
[CH3:1]C1C=CC(C(NC2C(C)=CC=CC=2C)=N)=CC=1.[CH2:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]=[C:29]([NH:37][P:38]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1)[CH2:20][CH3:21].C([Li])CCC.CI>>[CH2:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]=[C:29]([N:37]([P:38]([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH3:1])[C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1)[CH2:20][CH3:21]

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 67297631N'-(2-n-propylphenyl)-N-(diphenylphosphino)-4-methylbenzamidineHCID 178418339ButyllithiumHCID 178425630HCID 178425630, compound

Product 1

HCID 67308428N'-(2-n-propylphenyl)-N-(diphenylphosphino)-N-methyl-4-methylbenzamidine

Procedure

Procedure as described for NSP Amidine III using the following amounts: 1.42 g of N′-(2-n-propylphenyl)-N-(diphenylphosphino)-4-methylbenzamidine (3.0 mmol), 1.50 mL of 2.0 M butyllithium (15.0 mmol), 1.50 mL of 2.0 M methyliodide (3.0 mmol). Following removal of lithium iodide via filtration and removal of solvent in vacuo, a yellow sticky residue was recovered (1.63 g, 67%).

Workup

  1. customremoval of lithium iodide
  2. filtrationvia filtration and removal of solvent in vacuo
  3. customa yellow sticky residue was recovered (1.63 g, 67%)

Sources & evidence

ORD record
ord-88775628eef8434c880cb101af870824
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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