Hydrochloric Acid → 1-(4-Chlorophenyl)-1H-pyrrole-2,5-dione

HRID 1784042ノート

反応式

HRID 1784042 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](/[CH:11]=[CH:12]\[C:13]([OH:15])=O)=[O:10])=[CH:4][CH:3]=1.C[Si](N[Si](C)(C)C)(C)C.Cl>C1C=CC=CC=1.[Cl-].[Cl-].[Zn+2]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:9](=[O:10])[CH:11]=[CH:12][C:13]2=[O:15])=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 13838HexamethyldisilazaneHCID 5356193AF-794/00086051

生成物 1

HCID 154001-(4-Chlorophenyl)-1H-pyrrole-2,5-dione収率 97%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 241Benzene溶媒

実験手順

In Analogy to the procedure given in Mhaske et al., Synthesis, 2003, p863-870: A solution of 65 g (288 mmol) of (Z)-3-(4-chloro-phenylcarbamoyl)-acrylic acid in 300 ml of benzene was treated with 41.2 g (302 mmol) of zinc dichloride, dropwise with 90.1 ml (432 mmol) of bis(trimethylsilyl)amine and refluxed during 5 hrs. The mixture was poured into 300 ml of aqueous HCl (0.5 M). The aqueous phase was extracted with AcOEt, the combined organic phases were washed successively with saturated aqueous NaHCO3 and brine, and finally dried over Na2SO4. Evaporation of the solvent gave 58 g (97%) of the title compound. Brown amorphous solid. MS: 208 (M+H)+.

後処理

  1. customIn Analogy to the procedure given in Mhaske et al., Synthesis, 2003, p863-870
  2. temperaturerefluxed during 5 hrs
  3. extractionThe aqueous phase was extracted with AcOEt
  4. washthe combined organic phases were washed successively with saturated aqueous NaHCO3 and brine
  5. dry with materialfinally dried over Na2SO4
  6. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-befc109c4e5b4818a83415c21aacd7d1
出典データセット
uspto-grants-2009_03
特許番号
US07501413B2

反応ノート

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