N,N'-Dimethylethylenediamine → HCID 58516570, compound

HRID 1468468Notes

Reaction equation

HRID 1468468 reaction equation
I[C:2]1[CH:14]=[C:13]([C:15]([CH3:22])([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:16])[CH:12]=[CH:11][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1.[C:23]([C:27]1[CH:28]=[CH:29][C:30]2[NH:31][C:32]3[C:37]([C:38]=2[CH:39]=1)=[CH:36][C:35]([C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:34][CH:33]=3)([CH3:26])([CH3:25])[CH3:24].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>[Cu]I.C1(C)C=CC=CC=1>[C:23]([C:27]1[CH:28]=[CH:29][C:30]2[N:31]([C:2]3[CH:14]=[C:13]([C:15]([CH3:22])([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:16])[CH:12]=[CH:11][C:3]=3[O:4][CH:5]3[CH2:10][CH2:9][CH2:8][CH2:7][O:6]3)[C:32]3[C:37]([C:38]=2[CH:39]=1)=[CH:36][C:35]([C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:34][CH:33]=3)([CH3:26])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 154692093,6-Di-tert-butyl-9H-carbazoleHCID 58516582HCID 58516582, compound

Product 1

HCID 58516570HCID 58516570, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Procedure

To a 50 mL three necked round bottom flask equipped with a stir bar and condenser under N2 atmosphere add 20 mL of dry toluene, 5.00 g (12.01 mmol) of 2-(2-iodo-4-(2,4,4-trimethylpentan-2-yl)phenoxy)tetrahydro-2H-pyran (P5), Preparation 5; 3.56 g (12.01 mmol) of 3,6-di-t-butyl carbazole (P1), Preparation 1; 0.488 g (2.56 mmol) of CuI, 7.71 g (36.22 mmol) of K3PO4, and 0.338 g (3.84 mmol) of N,N′-dimethylethylenediamine. Reflux the reaction mixture for 48 hours, cool it, filter it through a bed of silica gel, rinse the silica gel with tetrahydrofuran (THF), and concentrate the organics to give a crude residue. Crystallize the crude residue using acetonitrile to yield 4.57 g (67.01%) of (P6) as a white solid.

Workup

  1. additionadd
  2. temperatureReflux the reaction mixture for 48 hours
  3. temperaturecool it
  4. filtrationfilter it through a bed of silica gel
  5. washrinse the silica gel with tetrahydrofuran (THF)
  6. concentrationconcentrate the organics

Sources & evidence

ORD record
ord-75fa20a9df3c4c7d8e74cdaa6eb57541
Source dataset
uspto-grants-2015_04
Patent number
US09000108B2

Reaction notes

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