N-Methylaniline → 5-chloro-2-[3-(N-methylanilino)propyl]-3-phenylisoindole-1-carboxylic acid ethyl ester

HRID 372334ノート

反応式

HRID 372334 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][CH2:24]OS(C)(=O)=O)[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]2[C:14]=1[CH:13]=[CH:12][C:11]([Cl:15])=[CH:10]2)=[O:5])[CH3:2].[CH3:30][NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C)P(=O)(N(C)C)N(C)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][CH2:24][N:31]([CH3:30])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]2[C:14]=1[CH:13]=[CH:12][C:11]([Cl:15])=[CH:10]2)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 7515N-MethylanilineHCID 54315092HCID 54315092、化合物

生成物 1

HCID 539973495-chloro-2-[3-(N-methylanilino)propyl]-3-phenylisoindole-1-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 12679Hexamethylphosphoramide溶媒

実験手順

A solution of 4.36 g. of 5-chloro-2-{3-[(methylsulfonyl)oxy]propyl}-3-phenylisoindole-1-carboxylic acid ethyl ester in 25 ml. of hexamethylphosphoric acid triamide is treated with 25 ml. of N-methylaniline and heated at 80° C. for 24 hours. The mixture is then evaporated to dryness under reduced pressure, and the residue treated with 250 ml. of ice-water. The oily precipitate is taken up in methylene chloride and the extract washed with a saturated solution of sodium chloride, dried over sodium sulfate and concentrated to dryness. The resulting oil is purified by chromatography on 150 g. of aluminum oxide [neutral; Brockmann activity I]. By elution with methylene chloride and evaporation of the solvent, there is obtained 5-chloro-2-[3-(N-methylanilino)propyl]-3-phenylisoindole-1-carboxylic acid ethyl ester; melting point 108°-110° C. Crystallization from ether/hexane gives almost colorless crystals of the same melting point.

後処理

  1. customThe mixture is then evaporated to dryness under reduced pressure
  2. additionthe residue treated with 250 ml
  3. washthe extract washed with a saturated solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe resulting oil is purified by chromatography on 150 g
  7. washBy elution
  8. customwith methylene chloride and evaporation of the solvent

出典と根拠

ORDレコード
ord-3ce753987ec24d5c90b42079b9bd8a14
出典データセット
uspto-grants-1978_05
特許番号
US04090027

反応ノート

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