Hydrochloric Acid → HCID 15086642、化合物

HRID 359102ノート

反応式

HRID 359102 の反応式
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.O=[C:10]1[CH2:14][CH2:13][CH2:12][CH:11]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(B)#N.[Na].Cl>C1C=CC=CC=1.CO>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4][CH:3]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 521998p-Toluenesulfonic acid monohydrateHCID 101953985CID 101953985

生成物 1

HCID 15086642HCID 15086642、化合物

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 887Methanol溶媒

実験手順

p-Chloroaniline (4 g), ethyl 2-oxocyclopentanecarboxylate (4.66 ml) and p-toluenesulfonic acid hydrate (0.66 g) were dissolved in benzene (80 ml), and the mixture was subjected to dehydrating condensation reaction under refluxing for 24 hours, and the mixture was allowed to cool. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give an oily product. This oily product was dissolved in absolute methanol (60 ml) and thereto was added sodium cyanoboron hydride (13.2 g) with stirring at room temperature in 10 portions over a period of 11 days. The reaction mixture was cooled with ice and thereto was added conc. hydrochloric acid (21 ml), and the mixture was concentrated under reduced pressure. Water and ethyl acetate were added to the resultant to separate into layers. The organic layer was washed with water 3 tlmes, and concentrated again under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixed solvent of chloroform/methanol [100:1 (v/v)] to give the oily desired product (3.76 g).

後処理

  1. customcondensation reaction
  2. temperatureunder refluxing for 24 hours
  3. temperatureto cool
  4. customThe insoluble material was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto give an oily product
  7. temperatureThe reaction mixture was cooled with ice
  8. concentrationthe mixture was concentrated under reduced pressure
  9. additionWater and ethyl acetate were added to the resultant
  10. customto separate into layers
  11. washThe organic layer was washed with water 3 tlmes
  12. concentrationconcentrated again under reduced pressure
  13. washeluted with a mixed solvent of chloroform/methanol [100:1 (v/v)]

出典と根拠

ORDレコード
ord-470ac121d6f944fd8c78f1cf75cd98e8
出典データセット
uspto-grants-1991_03
特許番号
US04999378

反応ノート

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