Water → HCID 59497548, 화합물

HRID 1747348노트

반응식

HRID 1747348 반응식
[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])([CH3:3])=[CH2:2].[C:14]([O:18][CH3:19])(=[O:17])[CH:15]=[CH2:16].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.O>CN(C=O)C.C(OCC)(=O)C>[CH3:19][O:18][C:14](=[O:17])[CH2:15][CH2:16][N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:4]([C:1]([CH3:3])=[CH2:2])[C:5]1=[O:13]

참가 물질

7

반응물 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-one

생성물 1

HCID 59497548HCID 59497548, 화합물수율 64.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 1-Isopropenyl-1,3-dihydro-benzimidazol-2-one (5 g, 28.7 mmol) in DMF (20 ml) was added methyl acrylate (2.8 ml, 31.6 mmol) followed by benzyltrimethylammonium hydroxide (Triton B, 40 wt % in MeOH, 3.2 ml). The resulting solution was stirred at ambient temperature until the reaction was complete. After this time the reaction was poured into water and ethyl acetate. The layers were separated and the aqueous phase was extracted twice more with ethyl acetate. The combined organic layers were dried (MgSO4), filtered and concentrated to give the crude product which was purified via column chromatography (silica gel, 30% ethyl acetate/hexanes). The product-containing fractions were combined and concentrated to give 4.8 g (64%) of the desired product.

후처리

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted twice more with ethyl acetate
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product which
  7. customwas purified via column chromatography (silica gel, 30% ethyl acetate/hexanes)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5091dcab4ef04cf985a939226adf33f5
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150556B2

반응 노트

불러오는 중…