2-Methylimidazoline → 2-Methyl-1-[(2,6-dimethylphenyl)carbamoylmethyl]-2-imidazoline

HRID 1649144Notes

Reaction equation

HRID 1649144 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]([CH2:12]Cl)=[O:11].[CH3:14][C:15]1[NH:19][CH2:18][CH2:17][N:16]=1>[N+](C)([O-])=O>[CH3:14][C:15]1[N:19]([CH2:12][C:10](=[O:11])[NH:9][C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:8])[CH2:18][CH2:17][N:16]=1

Participants

4

Reactant 2

HCID 107982-MethylimidazolineHCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamide

Product 1

HCID 130512442-Methyl-1-[(2,6-dimethylphenyl)carbamoylmethyl]-2-imidazoline

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

To a solution of 10.0 gm. (0.05 M) of 2-chloro-2',6'-acetoxylidide in 100 ml. of nitromethane add 21.35 gm (0.254 M) of lysidine. Stir the solution at room temperature for about 17 hours. Follow the progress of the reaction by thin layer chromatography on silica gel (acetonitrile:ammonium hydroxide:methanol, 85:10:5). At the completion of the reaction, remove the solvent in vacuo, to the residue add 150 ml. of water, adjust the pH to about 7.0 with conc. hydrochloric acid. Extract the resultant solution with 3×100 ml. methylene chloride and discard. Adjust the pH of the water layer to about 11-11.5 with 50% sodium hydroxide. Extract with 4×200 ml. of methylene chloride. Take the combined latter extracts and wash 3×50 ml. of water. Dry the methylene chloride extracts over Na2SO4. Evaporate the solvents to provide the title compound.

Workup

  1. customthe progress of the reaction by thin layer chromatography on silica gel (acetonitrile:ammonium hydroxide:methanol, 85:10:5)
  2. customAt the completion of the reaction
  3. customremove the solvent in vacuo
  4. additionto the residue add 150 ml
  5. extractionExtract the resultant solution with 3×100 ml
  6. extractionExtract with 4×200 ml
  7. washwash 3×50 ml
  8. dry with materialDry the methylene chloride
  9. customEvaporate the solvents

Sources & evidence

ORD record
ord-1470b4cb609d469895a4851d07d902f2
Source dataset
uspto-grants-1983_11
Patent number
US04415587

Reaction notes

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