Dodecane → HCID 847897, compound

HRID 2179169Notes

Reaction equation

HRID 2179169 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N.I[C:18]1[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][C:27]1=[O:31].CCCCCCCCCCCC>[Cu]I.O1CCOCC1>[CH3:24][C:22]1[CH:23]=[C:18]([N:26]2[CH2:30][CH2:29][CH2:28][C:27]2=[O:31])[CH:19]=[C:20]([CH3:25])[CH:21]=1

Participants

8

Reactant 5

HCID 8182DodecaneHCID 120252-PyrrolidoneHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 847897HCID 847897, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

An oven-dried resealable Schlenk tube was charged with CuI (2.0 mg, 0.0105 mmol, 1.0 mol %) and K3PO4 (450 mg, 2.12 mmol) under air. trans-1,2-Cyclohexanediamine (13 μL, 0.108 mmol, 10 mol %), 5-iodo-m-xylene (150 μL, 1.04 mmol), 2-pyrrolidinone (94 μL, 1.24 mmol) and dioxane (1.0 mL) were added under air. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 23 h. The resulting brown suspension was cooled to room temperature, dodecane (235 μL, GC standard) was added, and the mixture was filtered through a Celite pad eluting with ethyl acetate. The GC analysis of the filtrate indicated a 95% yield of the product.

Workup

  1. customThe Schlenk tube was sealed
  2. temperatureThe resulting brown suspension was cooled to room temperature
  3. filtrationthe mixture was filtered through a Celite pad
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-04b6627db9c44d7a8e496f99fa281e46
Source dataset
uspto-grants-2015_06
Patent number
US09067955B2

Reaction notes

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