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

HRID 223385Notes

Reaction equation

HRID 223385 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])/[CH:11]=[CH:12]/[CH3:13].[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]([CH:12]([CH3:13])[CH2:11][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 6061099N-(2,6-dimethylphenyl)crotonamide

Product 1

HCID 204806282-Methyl-1-[1-methyl-2-[(2,6-dimethylphenyl)carbamoyl]ethyl]-2-imidazoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 1.89 gm. (0.01 M) N-(2,6-dimethylphenyl)crotonamide, 0.90 gm. (0.0107 M) lysidine, 0.01 gm. (~0.001 M) methanesulphonic acid and about 40 ml. of ethanol in a pressure bottle and heat (bath temp. 100°-110° C.) for about 100 hours. Remove the solvent in vacuo, add about 50 ml. of water. Adjust the pH to 8.0 with concentrated HCl, and extract the aqueous phase with 2×25 ml. methylene chloride. Then adjust the aqueous phase to pH 13 with 50% sodium hydroxide and extract with 3×30 ml. of methylene chloride. Wash the combined methylene chloride extracts with 2×5 ml. of water. Dry the methylene chloride extracts over sodium sulfate. Evaporate off the solvents to obtain the title compound.

Workup

  1. customRemove the solvent in vacuo
  2. additionadd about 50 ml
  3. extractionextract the aqueous phase with 2×25 ml
  4. extractionextract with 3×30 ml
  5. washWash the combined methylene chloride
  6. dry with materialDry the methylene chloride
  7. customEvaporate off the solvents

Sources & evidence

ORD record
ord-96edf798c4604c18b309536b044217db
Source dataset
uspto-grants-1982_10
Patent number
US04353921

Reaction notes

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