Hydrochloric Acid → 3-(2,6-Dichloropyridin-4-yl)-1-methyl-imidazolidine-2,4-dione

HRID 489225

반응식

HRID 489225 반응식
Cl.C(O[C:5](=[O:9])[CH2:6][NH:7][CH3:8])C.[Cl:10][C:11]1[CH:16]=[C:15]([N:17]=[C:18]=[O:19])[CH:14]=[C:13]([Cl:20])[N:12]=1>C(Cl)Cl>[Cl:10][C:11]1[CH:16]=[C:15]([N:17]2[C:5](=[O:9])[CH2:6][N:7]([CH3:8])[C:18]2=[O:19])[CH:14]=[C:13]([Cl:20])[N:12]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 95849Glycine, N-methyl-, ethyl esterHCID 27816582,6-Dichloro-4-isocyanatopyridine

생성물 1

HCID 220253053-(2,6-Dichloropyridin-4-yl)-1-methyl-imidazolidine-2,4-dione수율 155.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
5 °C

실험 절차

TEA (7.2 ml, 51 mmol) was added to a suspension of the HCl salt of sarcosine ethyl ester (3.4 g, 24.5 mmol) in dry DCM (80 ml). The formed triethylamine hydrochloride was filtered off and rinsed with DCM (20 ml). The filtrate was transferred into a 3-necked round bottom flask and cooled to 5° C. A solution of 2,6-dichloropyridin-4-yl isocyanate (10 g, 53 mmol) in DCM (25 ml) was added dropwise over 10 min while keeping the inner temperature below 10° C. After 96 h at RT, the reaction mixture was refluxed for 10 h. After cooling to RT, the solution was washed with brine, dried over MgSO4 and concentrated. The obtained amorphous solid was chromatographed over silica gel (eluent: cyclohexane/EtOAc 80/20 to 50/50) to yield the above titled compound as a white solid (9.9 g). mp=134° C. 1H NMR (CDCl3): 7.75 (2H, s), 4.07 (2H, s), 3.10 (3H, s).

후처리

  1. filtrationThe formed triethylamine hydrochloride was filtered off
  2. washrinsed with DCM (20 ml)
  3. customThe filtrate was transferred into a 3-necked round bottom flask
  4. customthe inner temperature below 10° C
  5. temperaturethe reaction mixture was refluxed for 10 h
  6. temperatureAfter cooling to RT
  7. washthe solution was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe obtained amorphous solid was chromatographed over silica gel (eluent: cyclohexane/EtOAc 80/20 to 50/50)

출처 및 근거

ORD 기록
ord-b2921a2703f44893a9c8b09f9fc8e9c8
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977267B2

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