Benzyl Isothiocyanate → 3-Benzyl-1-methyl-2-thioxoimidazolidin-4-one

HRID 2121957Notes

Reaction equation

HRID 2121957 reaction equation
Cl.CO[C:4](=[O:8])[CH2:5][NH:6][CH3:7].C1CCN2C(=NCCC2)CC1.[CH2:20]([N:27]=[C:28]=[S:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)C>[CH2:20]([N:27]1[C:4](=[O:8])[CH2:5][N:6]([CH3:7])[C:28]1=[S:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 2346Benzyl IsothiocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)

Product 1

HCID 219376293-Benzyl-1-methyl-2-thioxoimidazolidin-4-oneYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sarcosine methyl ester hydrochloride (0.56 g, 4.0 mmol) and DBU (0.60 mL, 4.0 mmol) in anhydrous ethanol added benzyl isothiocyanate (0.53 mL, 4.0 mmol). The resulting solution was heated at reflux 16 h, cooled, concentrated and chromatographed (silica gel, DCM) to give the title compound (0.88 g, quant.). 1H-NMR (CDCl3): δ 7.49-7.53 (2H, m), 7.28-7.35 (3H, m), 5.02 (2H, s), 4.03 (2H, s), 3.34 (3H, s).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux 16 h
  3. temperaturecooled
  4. concentrationconcentrated
  5. customchromatographed (silica gel, DCM)

Sources & evidence

ORD record
ord-566add14f0be4d398821deabb1b039d8
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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