Chlorodiphenylphosphine → HCID 178425655, compound

HRID 925035Notes

Reaction equation

HRID 925035 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:16])=[NH:7])=[CH:4][CH:3]=1.C([Li])CCC.Cl[P:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:16])=[N:7][P:25]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 66180ChlorodiphenylphosphineHCID 178418339ButyllithiumHCID 178425630HCID 178425630, compound

Product 1

HCID 178425655HCID 178425655, compound

Procedure

Procedure as described for NP Amidine I using the following amounts: 1.19 g of 4-methyl-N1-(2,6-dimethylphenyl)benzamidine (Amidine III, 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 1.64 g (78%) 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 1.64 g (78%)
  9. customafter drying

Sources & evidence

ORD record
ord-394286a4b83f40aeb9a31a1ac09c069a
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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