Potassium Carbonate → 1-(4-Trifluoromethylphenyl)imidazolidin-2-one

HRID 600932ノート

反応式

HRID 600932 の反応式
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)=[O:6].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:15][C:14]([F:17])([F:16])[C:11]1[CH:12]=[CH:13][C:8]([N:7]2[CH2:2][CH2:3][NH:4][C:5]2=[O:6])=[CH:9][CH:10]=1

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 2563241-(2-Chloroethyl)-3-[4-(trifluoromethyl)phenyl]urea

生成物 1

HCID 106809511-(4-Trifluoromethylphenyl)imidazolidin-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of methyl 4-trifluoromethylaniline (3.47 g, 21.6 mmol) in dry toluene (50 mL) was added 2-chloroethylisocyante (2.50 g, 2.02 mL, 23.7 mmol). The mixture was stirred at 40° C. for 12 h. After cooling to room temperature, the solid was collected by filtration and washed with toluene, water and dried in air to provide 1-(2-chloro-ethyl)-3-(4-trifluoromethylphenyl)urea [5.28 g, 92.0%, >95% pure by LC/MS MS (ES+) m/z: 267, 269]. The urea (5.27 g, 23.7 mmol) was then stirred in DMF (50.0 mL) with K2CO3 (3.27 g, 11.98 mmol) at room temperature for 12 h. The solid was filtered off and the solvent was removed in vacuum. The crude product was dissolved in dichloromethane and passed through a silica column (50 g) and eluted with dichloromethane:ethyl acetate, 8:2 to give pure cyclic urea intermediate, 1-(4-trifluoromethylphenyl)imidazolidin-2-one, as white crystalline material (3.85 g, 84.7%). MS (ES+) m/z: 231.

後処理

  1. filtrationThe solid was filtered off
  2. customthe solvent was removed in vacuum
  3. dissolutionThe crude product was dissolved in dichloromethane
  4. washeluted with dichloromethane

出典と根拠

ORDレコード
ord-df41237eb6fa4b69910f1c7eacca0b9f
出典データセット
uspto-grants-2011_03
特許番号
US07902241B2

反応ノート

読み込み中…