Chloroform → HCID 12919023, compound

HRID 903157Notes

Reaction equation

HRID 903157 reaction equation
[CH3:1][C:2]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]1[NH:7][CH2:8][CH2:9][N:10]=1.C(Cl)(Cl)Cl.[CH3:20][S:21](Cl)(=[O:23])=[O:22].CC1(C)CCCN(C)C1(C)C>CCOCC>[CH3:20][S:21]([N:10]1[CH2:9][CH2:8][N:7]=[C:6]1[CH2:5][O:4][C:3]1[CH:11]=[CH:12][CH:13]=[C:14]([CH3:15])[C:2]=1[CH3:1])(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 6212Chloroform2×HCID 31297Methanesulfonyl chlorideHCID 498352-[(2,3-Dimethylphenoxy)methyl]-4,5-dihydro-1H-imidazoleHCID 21521028HCID 21521028, compound

Product 1

HCID 12919023HCID 12919023, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-(2,3-Dimethylphenoxymethyl)-2-imidazoline (8.0 g; 0.0392 moles) was dissolved in dry ether (75 ml) and sufficient dry chloroform (50 ml) and the solution cooled in ice (sufficient chloroform was used to prevent precipitation of the imidazoline on cooling). Methanesulphonyl chloride (4.50 g; 0.0393 moles) was added dropwise to the cold, stirred solution. When the addition was complete pentamethylpiperidine (6.08 g; 0.0392 moles) was added and the reaction mixture heated under reflux until tlc showed that reaction was complete (~3 hrs). The reaction mixture was then concentrated under reduced pressure and the residue extracted with a water/chloroform mixture (1:1; ~100 ml). The chloroform layer was washed with water, dried over magnesium sulphate and evaporated under reduced pressure to give a residue which was recrystallised from isopropanol to give 1-methanesulphonyl-2-(2,3-dimethylphenoxymethyl)-2-imidazoline, m.p. 142°-143° C.

Workup

  1. customprecipitation of the imidazoline
  2. temperatureon cooling)
  3. additionWhen the addition
  4. additionwas added
  5. temperaturethe reaction mixture heated
  6. temperatureunder reflux until tlc
  7. customshowed that reaction
  8. custom(~3 hrs)
  9. concentrationThe reaction mixture was then concentrated under reduced pressure
  10. extractionthe residue extracted with a water/chloroform mixture (1:1; ~100 ml)
  11. washThe chloroform layer was washed with water
  12. dry with materialdried over magnesium sulphate
  13. customevaporated under reduced pressure
  14. customto give a residue which
  15. customwas recrystallised from isopropanol

Sources & evidence

ORD record
ord-7f3c07284fb34c2a88d7a0e2da16cc9e
Source dataset
uspto-grants-1980_10
Patent number
US04226876

Reaction notes

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