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

HRID 600932노트

반응식

HRID 600932 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-df41237eb6fa4b69910f1c7eacca0b9f
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902241B2

반응 노트

불러오는 중…