N-Methylethylenediamine → HCID 847897, compound

HRID 1883467Notes

Reaction equation

HRID 1883467 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[NH:10]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15].CN[CH2:18][CH2:19]N>[Cu]I>[I:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH:3]=1.[NH:10]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15].[CH3:11][CH2:12][CH2:13][CH2:18][CH2:19][CH2:7][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:8].[CH3:8][C:6]1[CH:7]=[C:2]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:3]=[C:4]([CH3:9])[CH:5]=1

Participants

8

Reactant 3

HCID 8014N-MethylethylenediamineHCID 120252-PyrrolidoneHCID 1409241-Iodo-3,5-dimethylbenzene

Product 4

HCID 8182DodecaneHCID 120252-PyrrolidoneHCID 1409241-Iodo-3,5-dimethylbenzeneHCID 847897HCID 847897, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
60 °C

Procedure

A test tube with a screw thread was equipped with a 10×3 mm Teflon-coated stirring bar and charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %) and K5P3O10 (Strem, finely ground, 430 mg, 0.96 mmol). The test tube was closed with an open-top screw cap fitted with a Teflon-lined silicon rubber septum, evacuated through a 21-gauge needle, and then backfilled with argon. Meanwhile, a stock solution of 5-iodo-m-xylene (2.16 mL), 2-pyrrolidinone (1.40 mL), and dodecane (internal GC standard, 0.68 mL) in toluene (15 mL) was prepared in a 25 mL pear-shaped flask under argon. A portion of the stock solution (1.28 mL) containing 1.0 mmol of 5-iodo-m-xylene and 1.2 mmol of 2-pyrrolidinone was added using a syringe, followed by N-methylethylenediamine (8.9 μL, 1.0 mmol, 10 mol %). The reaction mixture in the test tube was stirred in a 60±5° C. oil bath for 5 h. The test tube was then allowed to reach room temperature, the screw cap was removed, and ethyl acetate (2 mL) was added. A 50-100 μL sample of the supernatant solution from the test tube was diluted with ethyl acetate (1 mL). GC analysis of the resulting solution indicated a 95% yield of N-(3,5-dimethylphenyl)-2-pyrrolidinone.

Workup

  1. customThe test tube was closed with an open-top screw
  2. customcap
  3. customevacuated through a 21-gauge needle
  4. additionwas added
  5. customto reach room temperature
  6. customthe screw cap
  7. customwas removed
  8. additionethyl acetate (2 mL) was added
  9. additionA 50-100 μL sample of the supernatant solution from the test tube was diluted with ethyl acetate (1 mL)

Sources & evidence

ORD record
ord-43a928ba4e014a48ae95e4298ffac496
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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