Chlorodiphenylphosphine → HCID 178483811, compound

HRID 925050Notes

Reaction equation

HRID 925050 reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][NH:5][C:6](=[NH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([Li])CCC.Cl[P:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][NH:5][C:6](=[N:13][P:21]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 66180ChlorodiphenylphosphineHCID 178418339ButyllithiumHCID 178483800HCID 178483800, compound

Product 1

HCID 178483811HCID 178483811, compound

Procedure

Procedure as described for NP Amidine I using the following amounts and modifications: 0.956 g of N1-(2-(dimethylamino)ethyl)benzamidine (Amidine XII, 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 oily product was treated with 20 mL of pentane. After 1 hour stiffing at room temperature, a white solid formed. The solution was concentrated to approximately 10 mL and filtered while cold, yielding 0.891 g (47%) after drying.

Workup

  1. filtrationAfter filtration
  2. customto remove
  3. customlithium chloride and removal of solvent
  4. additionthe oily product was treated with 20 mL of pentane
  5. customa white solid formed
  6. concentrationThe solution was concentrated to approximately 10 mL
  7. filtrationfiltered while cold,
  8. customyielding 0.891 g (47%)
  9. customafter drying

Sources & evidence

ORD record
ord-504133c5c84544a18118f8ab16fdae79
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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