Triethylamine → Pyrene

HRID 2425373Notes

Reaction equation

HRID 2425373 reaction equation
C(O)(=O)COCCOCC(O)=O.C(Cl)(=O)C(Cl)=O.N[C:20]1[C:33]2[C:34]3=[C:35]4[C:30](=[CH:31][CH:32]=2)[CH:29]=[CH:28][CH:27]=[C:26]4[CH:25]=[CH:24][C:23]3=[CH:22][CH:21]=1.C(N(CC)CC)C>ClCCl.CN(C=O)C>[CH:27]1[C:26]2[C:35]3=[C:34]4[C:23](=[CH:24][CH:25]=2)[CH:22]=[CH:21][CH:20]=[C:33]4[CH:32]=[CH:31][C:30]3=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 153521-AminopyreneHCID 65578Oxalyl chlorideHCID 900393,6-Dioxaoctandioic acid

Product 1

HCID 31423PyreneYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

3,6-dioxaoctanedioic acid (0.28 mmol) was dispersed in 100 ml of dichloromethane (CH2Cl2) in which 0.1 ml of oxalyl chloride ((COCl)2) and 15 μl of DMF were added, to prepare a solution. After the solution was stirred at ambient temperature for 4 hours, volatiles were removed from the solution and the residue was re-dissolved in a small amount of dichloromethane. After the solution was added slowly to dichloromethane solution in which 152 mg (0.70 mmol) of 1-aminopyrene and 0.2 ml (1.4 mmol) of triethylamine were dissolved, the solution was reacted at ambient temperature for 4 hours and the volatiles were removed. And then, the resulting product was partitioned between water and dichloromethane and the organic phase was separated and washed with water; the solvent was removed from the obtained organic phase; and then, re-crystallization was carried out with a solvent combination of dichloromethane and methanol. The target product, a pyrene compound of 3,6-dioctanedioic acid was obtained (reddish green solid, yield: 65%).

Workup

  1. additionwere added
  2. customto prepare a solution
  3. customvolatiles were removed from the solution
  4. dissolutionthe residue was re-dissolved in a small amount of dichloromethane
  5. dissolutionwere dissolved
  6. customthe solution was reacted at ambient temperature for 4 hours
  7. customthe volatiles were removed
  8. customAnd then, the resulting product was partitioned between water and dichloromethane
  9. customthe organic phase was separated
  10. washwashed with water
  11. customthe solvent was removed from the obtained organic phase
  12. customand then, re-crystallization

Sources & evidence

ORD record
ord-214ed8ad436a42b89efc5be255d0de13
Source dataset
uspto-grants-2011_06
Patent number
US07964721B2

Reaction notes

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