Water → 1-Methyl-4-phenyl-1,3-dihydroimidazole-2-thione

HRID 537887Notes

Reaction equation

HRID 537887 reaction equation
Cl.[CH3:2][NH:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.[S-:13][C:14]#[N:15].[K+].O>C(O)(=O)C>[CH3:2][N:3]1[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:15][C:14]1=[S:13]

Participants

5

Reactant 3

HCID 962WaterHCID 516872Potassium thiocyanateHCID 122398392-Methylamino-1-phenyl-ethanone hydrochloride

Product 1

HCID 201464331-Methyl-4-phenyl-1,3-dihydroimidazole-2-thioneYield 47.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

An adaptation of the method reported by Kjellin and Sandström, Acta Chem. Scand. 1969, 23, 2879-2887 was used. A mixture of 2-methylamino-1-phenyl-ethanone hydrochloride (0.754 g, 4.06 mmol) (see e.g. Hyde et al. J. Am. Chem. Soc. 1928, 50, 2287-2292; Shang et al. Chem. Eur. J. 2007, 13, 7780-7784) and potassium thiocyanate (0.434 g, 4.46 mmol) in acetic acid (12 mL) was heated at 140° C. for 10 minutes using a microwave synthesizer. Dilution with water (50 mL) and cooling in an ice bath caused the product to precipitate. It was collected by filtration, washed with water, and vacuum dried to yield the title compound (0.365 g, 47%) pure as an off-white solid. 1H NMR (500 MHz, DMSO-d6): δ12.66 (br s, 1H), 7.65 (d, J=7.6 Hz, 2H), 7.60 (s, 1H), 7.39 (I, J=7.8 Hz, 2H), 7.27 (t, J=7.4 Hz, 1H), 3.49 (s, 3H).

Workup

  1. customto precipitate
  2. filtrationIt was collected by filtration
  3. washwashed with water, and vacuum
  4. customdried

Sources & evidence

ORD record
ord-a58faa188a4b411e9f6100033a51c3f2
Source dataset
uspto-grants-2014_10
Patent number
US08865711B2

Reaction notes

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