Methyl iodide → HCID 86649893, compound

HRID 1803117Notes

Reaction equation

HRID 1803117 reaction equation
[I:1]C.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([NH:17][C:18](N)=[S:19])[CH:8]=[CH:9][C:10]=1[N:11]1[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]1>C(O)C>[IH:1].[N:17]([C:7]1[CH:8]=[CH:9][C:10]([N:11]2[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]2)=[C:5]([O:4][CH3:3])[CH:6]=1)=[C:18]=[S:19]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 86649893HCID 86649893, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Step D (5): Iodomethane (0.066 mL, 1.07 mmol) was added to a solution of 1-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)thiourea (280 mg, 1.07 mmol) in absolute ethanol (5 mL). The resulting mixture was heated at 50° C. for 3 h. After cooling to rt, the reaction was concentrated in vacuo. The crude residue was purified using silica gel chromatography (0-10% MeOH/chloroform, linear gradient over 72 min, flow 25 mL/min) to afford 1-(4-isothiocyanato-2-methoxyphenyl)-4-methyl-1H-imidazole hydroiodide (135 mg, 46% yield) as a white solid. LC-MS (M+H)+ 277.2.

Workup

  1. temperatureAfter cooling to rt
  2. concentrationthe reaction was concentrated in vacuo
  3. customThe crude residue was purified
  4. customsilica gel chromatography (0-10% MeOH/chloroform, linear gradient over 72 min, flow 25 mL/min)

Sources & evidence

ORD record
ord-355d90b3845a4db2b87bf07b82bab2b4
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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