3-Bromoaniline → 3-(3-Bromophenylamino)-4-(4-chlorophenyl)-1H-pyrrole-2,5-dione

HRID 2084985ノート

反応式

HRID 2084985 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[C:10]1[C:11](=[O:23])[NH:12][C:13](=[O:22])[C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1>CO>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:10]2[C:11](=[O:23])[NH:12][C:13](=[O:22])[C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH:6]=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 115623-BromoanilineHCID 112879523-chloro-4-(4-chlorophenyl)-1H-pyrrole-2,5-dione

生成物 1

HCID 99516683-(3-Bromophenylamino)-4-(4-chlorophenyl)-1H-pyrrole-2,5-dione

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 3-bromoaniline (227 mL, 0.020 mol) and 3-chloro-4-(4-chlorophenyl)-1H-pyrrole-2,5-dione (2.02 g, 0.0083 mol; prepared by analogy with the methods described in WO97/34890 and Wiley, R P H, and Slaymaker, S. C. J. Am. Chem. Soc (80) 1385 (1958)) in methanol (50 mL) was heated at reflux for 40 hours, cooled and concentrated. The residue was acidified with aqueous hydrochloric acid (1M, 200 mL) and extracted with ethyl acetate (3×200 mL). The combined organic solutions were washed with water and brine, dried with magnesium sulphate, evaporated and the residue chromatographed on silica gel using dichloromethane-diethyl ether (gradient from 100:0 to 95:5 v/v) as eluent to afford the title compound as a solid.

後処理

  1. customprepared by analogy with the methods
  2. temperatureat reflux for 40 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. extractionextracted with ethyl acetate (3×200 mL)
  6. washThe combined organic solutions were washed with water and brine
  7. dry with materialdried with magnesium sulphate
  8. customevaporated
  9. customthe residue chromatographed on silica gel

出典と根拠

ORDレコード
ord-b98e98e237b141459aae2a73dbad1912
出典データセット
uspto-grants-2004_04
特許番号
US06719520B2

反応ノート

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