Chlorodiphenylphosphine → HCID 178424812, compound

HRID 925036Notes

Reaction equation

HRID 925036 reaction equation
[C:1]([C:5]1[CH:21]=[CH:20][C:8]([C:9]([NH:11][C:12]2[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:19])=[NH:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.Cl[P:28]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[C:1]([C:5]1[CH:21]=[CH:20][C:8]([C:9]([NH:11][C:12]2[C:13]([CH3:19])=[CH:14][CH:15]=[CH:16][C:17]=2[CH3:18])=[N:10][P:28]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 66180ChlorodiphenylphosphineHCID 178418339ButyllithiumHCID 178424805HCID 178424805, compound

Product 1

HCID 178424812HCID 178424812, compoundYield 93%

Procedure

Procedure as described for NP Amidine I using the following amounts: 1.40 g of 4-t-butyl-N1-(2,6-dimethylphenyl)benzamidine (Amidine IV, 5.0 mmol), 2.50 mL of 2.0 M butyllithium (5.0 mmol), 0.93 mL chlorodiphenylphosphine (5.0 mmol). After filtration to remove lithium chloride and removal of solvent, the sticky residue was treated with 20 mL of pentane. After 1 hour stirring at room temperature, the pentane was removed in vacuo yielding 2.16 g (93%) of off-white solid.

Workup

  1. filtrationAfter filtration
  2. customto remove
  3. customlithium chloride and removal of solvent
  4. additionthe sticky residue was treated with 20 mL of pentane
  5. customthe pentane was removed in vacuo

Sources & evidence

ORD record
ord-fd56bbbde4424956b64c5c6dfa6281bc
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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