N,N'-Dimethylurea → 4,5-bis(4-methoxyphenyl)-1,3-dimethyl-1H-imidazol-2(3H)-one

HRID 655386

반응식

HRID 655386 반응식
O[CH:2]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=O.[CH3:21][NH:22][C:23]([NH:25][CH3:26])=[O:24]>C(O)CO.O>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:22]([CH3:21])[C:23](=[O:24])[N:25]([CH3:26])[C:2]=2[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 7293N,N'-DimethylureaHCID 954154,4'-Dimethoxybenzoin

생성물 1

HCID 593548284,5-bis(4-methoxyphenyl)-1,3-dimethyl-1H-imidazol-2(3H)-one수율 68.5%

시약·촉매·용매 2

HCID 174Ethylene Glycol용매HCID 962Water용매

반응 조건

온도
180 °C

실험 절차

A mixture of 2-hydroxy-1,2-bis(4-methoxyphenyl)ethanone (1 g, 3.6 mmol) and 1,3-dimethylurea (1.29 g, 14.7 mmol) in ethylene glycol (10 mL) was refluxed at 180° C. for 2 h. The reaction mixture was diluted with water and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water, dried over Na2SO4, filtered and then concentrated in vacuo. The crude material was purified via silica gel column chromatography eluting with 80% EtOAc in hexanes to afford 4,5-bis(4-methoxyphenyl)-1,3-dimethyl-1H-imidazol-2(3H)-one (0.8 g, 67%) as a solid.

후처리

  1. extractionextracted with EtOAc (2×50 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified via silica gel column chromatography
  7. washeluting with 80% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-2c14093d19aa4c4790443352bc3178ce
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071595B2

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