Chlorodiphenylphosphine → HCID 178420371, compound

HRID 925055Notes

Reaction equation

HRID 925055 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7](=[NH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=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>CCCCC>[C:28]1([P:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:14]=[C:7]([NH:6][C:2]2[S:1][CH:5]=[CH:4][N:3]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 66180ChlorodiphenylphosphineHCID 178418339ButyllithiumHCID 178512080HCID 178512080, compound

Product 1

HCID 178420371HCID 178420371, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

Procedure as described for NP Amidine XVII using the following amounts: 3.06 g of N1-(thiazol-2-yl)benzamidine (Amidine XVI, 15.0 mmol), 7.50 mL of 2.0 M butyllithium (15.0 mmol), 0.93 mL of chlorodiphenylphosphine (15.0 mmol). Following removal of lithium chloride, the solvent was removed from the filtrate to give a sticky residue. The sticky residue was suspended in 100 mL of pentane. Vigorous stirring and scraping eventually yielded an off-white solid after 2 hours. The solid was collected and dried (2.59 g). The lithium chloride solid separated from reaction solution was extracted with 100 mL of diethylether, filtered, taken to dryness, and treated with 100 mL of pentane. Stirring and scraping produced white solid that was collected and dried yielding an additional 1.56 g of solid. Combined yield 4.15 g (71%).

Workup

  1. customremoval of lithium chloride
  2. customthe solvent was removed from the filtrate
  3. customto give a sticky residue
  4. customscraping eventually yielded an off-white solid after 2 hours
  5. customThe solid was collected
  6. customdried (2.59 g)
  7. customThe lithium chloride solid separated from reaction solution
  8. extractionwas extracted with 100 mL of diethylether
  9. filtrationfiltered
  10. additiontreated with 100 mL of pentane
  11. stirringStirring
  12. customscraping produced white solid
  13. customthat was collected
  14. customdried

Sources & evidence

ORD record
ord-d3f6520c8e5345d2aa59e0ad19173175
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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