Water → HCID 59497548、化合物

HRID 1747348ノート

反応式

HRID 1747348 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 59497548HCID 59497548、化合物収率 64.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5091dcab4ef04cf985a939226adf33f5
出典データセット
uspto-grants-2015_10
特許番号
US09150556B2

反応ノート

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