Hydrochloric Acid → 3-(3,5-Dichlorophenyl)-2-thioxoimidazolidin-4-one

HRID 489221Notes

Reaction equation

HRID 489221 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[S:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.[NH2:13][CH2:14][C:15](OCC)=[O:16]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:15](=[O:16])[CH2:14][NH:13][C:10]2=[S:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12176Glycine ethyl esterHCID 1387763,5-Dichlorophenyl isothiocyanate

Product 1

HCID 220253023-(3,5-Dichlorophenyl)-2-thioxoimidazolidin-4-oneYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,5-Dichlorophenylisothiocyanate (5 g, 24.5 mmol) was added by portion to a suspension of the HCl salt of ethyl glycinate (3.4 g, 24.5 mmol) in a mixture of TEA (7.5 ml, 53.9 mmol) and dry DCM (40 ml) while cooling the flask in a water bath. After 60 h at RT, the solution was concentrated to dryness and partitioned between EtOAc and aqueous HCl. The organic layer was washed with water and concentrated. The obtained amorphous solid was washed with Et2O to yield 3-(3,5-dichlorophenyl)-2-thioxoimidazolidin-4-one as an orange solid (5.3 g). 1H NMR (CDCl3): 7.45 (1H, m), 7.25 (2H, m), 4.44 (2H, s).

Workup

  1. temperaturewhile cooling the flask in a water bath
  2. concentrationthe solution was concentrated to dryness
  3. custompartitioned between EtOAc and aqueous HCl
  4. washThe organic layer was washed with water
  5. concentrationconcentrated
  6. washThe obtained amorphous solid was washed with Et2O

Sources & evidence

ORD record
ord-9a7556d4c565459e9af3ea24a6e5f63c
Source dataset
uspto-grants-2005_12
Patent number
US06977267B2

Reaction notes

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