Methyl iodide → HCID 18549466, compound

HRID 376433Notes

Reaction equation

HRID 376433 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:20][CH2:19][NH:18][C:17]2=[S:21])=[CH:12][CH:11]=1)([O-:9])=[O:8].IC.[C:24](OCC)(=O)C>CC(C)=O.O>[CH3:24][S:21][C:17]1[N:16]([C:13]2[CH:14]=[CH:15][C:10]([N+:7]([O-:9])=[O:8])=[CH:11][CH:12]=2)[CH:20]=[CH:19][N:18]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 53443425HCID 53443425, compound

Product 1

HCID 18549466HCID 18549466, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of potassium carbonate(40.07 g, 22.60 mmol) in 175 mL acetone was added 1-(4-nitrophenyl) imidazoline-2-thione(5.0 g,22.60 mmol). Dripped iodomethane (1.44 mL,23.05 mmol) into reaction mixture and heated to reflux temperature for 20 h. Concentrated reaction mixture under reduced pressure and took up resulting solid in 200 mL water. Extracted aqueous three times with ethyl acetate. Combined extracts, dried over magnesium sulfate and concentrated in vacuo to give 5.29 g of crude 4-(2'-methylthioimidazol-1-yl)nitrobenzene. 1HNMR(DMSO-d6) δ: 10.45 (s, 1 H) 8.06 (dd, 1 H, J1 =2.0 Hz, J2 =8.0 Hz), 8.38-8.33 (m, 2 H), 7.77-7.72 (m, 2 H), 7.61 (d, 1 H, J=1.5 Hz), 7.14 (d, 1 H, J=1.5 Hz), 2.52 (s, 3 H). ESI mass spectrum analysis m/z(relative intensity) 236 (M+H,100).

Workup

  1. temperatureheated
  2. temperatureto reflux temperature for 20 h
  3. concentrationConcentrated
  4. customreaction mixture under reduced pressure
  5. dry with materialCombined extracts, dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99cc6c9f84034fa8a0aceab5fa519053
Source dataset
uspto-grants-2000_02
Patent number
US06020357

Reaction notes

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