Diethyl Sulfate → HCID 15457414、化合物

HRID 1018776ノート

反応式

HRID 1018776 の反応式
[CH:1]([C:3]1[NH:4][C:5]([C:10]#[N:11])=[C:6]([C:8]#[N:9])[N:7]=1)=[CH2:2].[CH2:12](N(CC)CC)[CH3:13].S(OCC)(OCC)(=O)=O>C(OCC)(=O)C.C1COCC1.CCCCCC.C(OCC)(=O)C>[CH2:12]([N:7]1[C:6]([C:8]#[N:9])=[C:5]([C:10]#[N:11])[N:4]=[C:3]1[CH:1]=[CH2:2])[CH3:13]

参加物

7

反応物 3

HCID 6163Diethyl SulfateHCID 8471TriethylamineHCID 121131612-Ethenyl-1H-imidazole-4,5-dicarbonitrile

生成物 1

HCID 15457414HCID 15457414、化合物収率 65%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

A flask equipped with a magnetic stirbar was charged with 6.26 g of 2-vinyidicyanoimidazole. To this, 75 ml of distilled THF and 6.1 ml of triethylamine were added with stirring. After 5 minutes stirring, 5.7 ml of diethyl sulphate was added. This mixture was allowed to stir for 2 days. Analysis by TLC (50/50 hexane/ethyl acetate, UV visualization) showed the reaction was complete (starting material rf 0.3, product rf 0.6). The THF solution was rotovapped and the residue was dissolved in ethyl acetate. The ethyl acetate was washed with 10% aqueous sodium hydroxide. The combined aqueous layers were back extracted with methylene chloride. The combined organic layers were dried with magnesium sulphate and rotovapped to dryness. The crude residue was triturated with ether. The ether extracts were rotovapped and the residue recrystallized with ether/hexanes to yield 3.124 g of the product, mp 66-70° C. as yellow needles. A second crop yielded 1.72 g for a combined yield of 65%.

後処理

  1. customA flask equipped with a magnetic stirbar
  2. stirringAfter 5 minutes stirring
  3. stirringto stir for 2 days
  4. washThe ethyl acetate was washed with 10% aqueous sodium hydroxide
  5. extractionThe combined aqueous layers were back extracted with methylene chloride
  6. dry with materialThe combined organic layers were dried with magnesium sulphate
  7. customThe crude residue was triturated with ether
  8. customthe residue recrystallized with ether/hexanes

出典と根拠

ORDレコード
ord-cf5e280a241246df8223568f2d0c671e
出典データセット
uspto-grants-2002_11
特許番号
US06482954B2

反応ノート

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