Methanesulfonic Acid → 2-Methyl-1-[2-methyl-2-[(2,6-dimethylphenyl)carbamoyl]ethyl]-2-imidazoline

HRID 223386Notes

Reaction equation

HRID 223386 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[O:14])[C:11]([CH3:13])=[CH2:12].[CH3:15][C:16]1[NH:20][CH2:19][CH2:18][N:17]=1.CS(O)(=O)=O>C(O)C>[CH3:15][C:16]1[N:20]([CH2:12][CH:11]([CH3:13])[C:10](=[O:14])[NH:9][C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:8])[CH2:19][CH2:18][N:17]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 107982-MethylimidazolineHCID 296039N-(2,6-Dimethylphenyl)-2-methylprop-2-enamide

Product 1

HCID 204806302-Methyl-1-[2-methyl-2-[(2,6-dimethylphenyl)carbamoyl]ethyl]-2-imidazoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 30.0 gm. (0.16 M) N-(2,6-dimethylphenyl)-2-methylpropenamide [methacroyl-2',6'-xylidide], 13.3 gm. (0.16 M) lysidine, 3 gm. (0.03 M) methanesulphonic acid and 150 ml. of ethanol in a pressure bottle and heat at about 150° C. for about 48 hours. Remove the solvent in vacuo, add 200 ml. of water and adjust the pH to 7.8 with conc. HCl. Extract the aqueous phase with 4×100 ml. of methylene chloride and set these aside. Treat the aqueous phase with 20% NaOH to obtain a pH of about 13. Extract the aqueous phase with 4×100 ml. of methylene chloride. Wash the combined methylene chloride extracts with 3×10 ml. water and dry organic layer over sodium sulfate. Evaporate off the solvents to obtain the title compound.

Workup

  1. customRemove the solvent in vacuo
  2. additionadd 200 ml
  3. extractionExtract the aqueous phase with 4×100 ml
  4. additionTreat the aqueous phase with 20% NaOH
  5. customto obtain a pH of about 13
  6. extractionExtract the aqueous phase with 4×100 ml
  7. washWash the combined methylene chloride
  8. customEvaporate off the solvents

Sources & evidence

ORD record
ord-5266b27741fc4619bd3707faf8eee4f6
Source dataset
uspto-grants-1982_10
Patent number
US04353921

Reaction notes

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