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

HRID 489225

反応式

HRID 489225 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
5 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b2921a2703f44893a9c8b09f9fc8e9c8
出典データセット
uspto-grants-2005_12
特許番号
US06977267B2

関連ノート

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