Methyl iodide → HCID 18549466, compound

HRID 1266313Notes

Reaction equation

HRID 1266313 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, 1H) 8.06 (dd, 1H, J1=2.0 Hz, J2=8.0 Hz), 8.38-8.33 (m, 2H), 7.77-7,72 (m, 2H), 7.61 (d, 1H, J=1.5 Hz), 7.14 (d, 1H, J=1.5 Hz), 2.52 (s, 3H), 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-2980356e7a074f80bb7190da890b4d6f
Source dataset
uspto-grants-2003_04
Patent number
US06548512B1

Reaction notes

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