Toluene → HCID 58516561, compound

HRID 572951Notes

Reaction equation

HRID 572951 reaction equation
I[C:2]1[CH:7]=[C:6]([C:8]([CH3:15])([CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH3:9])[CH:5]=[CH:4][C:3]=1[O:16][CH2:17][O:18][CH3:19].[C:20]([C:24]1[CH:25]=[CH:26][C:27]2[NH:28][C:29]3[C:34]([C:35]=2[CH:36]=1)=[C:33](C(C)(C)C)[CH:32]=[CH:31][CH:30]=3)([CH3:23])([CH3:22])[CH3:21].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNCCNC.[C:55]1([CH3:61])[CH:60]=CC=C[CH:56]=1>C1COCC1.[Cu]I>[C:20]([C:24]1[CH:25]=[CH:26][C:27]2[N:28]([C:2]3[CH:7]=[C:6]([C:8]([CH3:15])([CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH3:9])[CH:5]=[CH:4][C:3]=3[O:16][CH2:17][O:18][CH3:19])[C:29]3[C:34]([C:35]=2[CH:36]=1)=[CH:33][C:32]([C:55]([CH3:61])([CH3:60])[CH3:56])=[CH:31][CH:30]=3)([CH3:21])([CH3:22])[CH3:23]

Participants

8

Reactant 5

HCID 1140TolueneHCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 58516558HCID 58516558, compoundHCID 66780410HCID 66780410, compound

Product 1

HCID 58516561HCID 58516561, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Heat a mixture of 4.96 g (13.18 mmol) of 2-iodo-1-(methoxymethoxy)-4-(2,4,4-trimethylpentan-2-yl)benzene (P3), Preparation 3; 3.68 g (13.18 mmol) of 3,5-di-t-butylcarbazole (P1), Preparation 1; 0.53 g (2.6 mmol) of CuI, 8.42 g (39.54 mmol) of K3PO4, and 0.63 g (4.13 mmol) of N,N′-dimethylethylenediamine in 25 mL of toluene under nitrogen atmosphere to reflux and reflux for 24 hours. Cool the reaction mixture, dilute it with 25 mL of THF, and filter to remove solid. Concentrate the filtrate to give a solid residue. Crystallize the solid residue from acetonitrile to yield 5.5 g (90%) of (P4) as white solid.

Workup

  1. temperatureHeat
  2. temperaturereflux for 24 hours
  3. temperatureCool the reaction mixture
  4. filtrationfilter
  5. customto remove solid
  6. concentrationConcentrate the filtrate
  7. customto give a solid residue
  8. customCrystallize the solid residue from acetonitrile
  9. customto yield 5.5 g (90%) of (P4) as white solid

Sources & evidence

ORD record
ord-ad325cf06f724ea597ed0b24a21069b7
Source dataset
uspto-grants-2015_05
Patent number
US09029487B2

Reaction notes

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