海萝胶 → 3-(2,6-Dichloropyridin-4-yl)-1-methyl-imidazolidine-2,4-dione

HRID 489225

反应方程式

HRID 489225 反应方程式
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

参与物

5

反应物 3

HCID 313海萝胶HCID 958492-(甲基氨基)乙酸乙酯HCID 27816582,6-二氯-4-吡啶异氰酸酯

产物 1

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

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂2 次

反应条件

温度
5 °C

实验过程

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).

后处理

  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)

来源与证据

ORD记录
ord-b2921a2703f44893a9c8b09f9fc8e9c8
来源数据集
uspto-grants-2005_12
专利号
US06977267B2

关联笔记

加载中…