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

HRID 1792857노트

반응식

HRID 1792857 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-31b9b3e14509464ea943b6c60dbf1524
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07078420B2

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