Ammonium thiocyanate → 4-Imidazolidinone, 1-(phenylmethyl)-2-thioxo-

HRID 1285333Notes

Reaction equation

HRID 1285333 reaction equation
[S-:1][C:2]#[N:3].[NH4+].C(O[C:8](=[O:18])[CH2:9][NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C>>[CH2:11]([N:10]1[CH2:9][C:8](=[O:18])[NH:3][C:2]1=[S:1])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 15666Ammonium thiocyanateHCID 80908N-Benzylglycine ethyl ester

Product 1

HCID 53685104-Imidazolidinone, 1-(phenylmethyl)-2-thioxo-Yield 57.9%

Procedure

Ammonium thiocyanate (47.27 g) and N-benzylglycine ethyl ester (40.0 g) were fused together at 140° C. for 4 hours. The deep red solution was allowed to cool to room temperature and the solid residue washed with ethanol/water (1:1) (200 ml). The solid was collected by filtration, washed with ethanol/water (1:1) (5×200 ml) and with diethyl ether (3×100 ml) to afford 1-benzyl-2-thiohydantoin (24.72 g), m.p. 150°-152° C.

Workup

  1. washthe solid residue washed with ethanol/water (1:1) (200 ml)
  2. filtrationThe solid was collected by filtration
  3. washwashed with ethanol/water (1:1) (5×200 ml) and with diethyl ether (3×100 ml)

Sources & evidence

ORD record
ord-ba905a9c42f846609c7a734fff586857
Source dataset
uspto-grants-1986_01
Patent number
US04567176

Reaction notes

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