Sodium Hydroxide → 5-(3,4-Dichlorophenylthio)pyrrole-3-carboxylic Acid

HRID 894030ノート

反応式

HRID 894030 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[NH:14][CH:13]=[C:12]([C:15]([O:17]C)=[O:16])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[NH:14][CH:13]=[C:12]([C:15]([OH:17])=[O:16])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 12897048Methyl 5-(3,4-Dichlorophenylthio)pyrrole-3-carboxylate

生成物 1

HCID 128970395-(3,4-Dichlorophenylthio)pyrrole-3-carboxylic Acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

Methyl 5-(3,4-dichlorophenylthio)pyrrole-3-carboxylate (1.7 g.) was combined with 20 ml. of methanol and 20 ml. of 1 N sodium hydroxide and refluxed for 3 hours. The methanol was allowed to evaporate, and approximately one volume of water was added to the aqueous residue, which was then extracted twice with ether, cooled in an ice-water bath, acidified with conc. hydrochloric acid, and the product extracted into ethyl acetate. The three ethyl acetate extracts were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a gummy solid which was crystallized by trituration with hexane and recovered by filtration (1.34 g., m.p. 156°-159° C.). Recrystallization from chloroform gave purified 5-(3,4-dichlorophenylthio)pyrrole-3-carboxylic acid (850 mg., m.p. 159°-161° C.).

後処理

  1. customto evaporate
  2. additionapproximately one volume of water was added to the aqueous residue, which
  3. extractionwas then extracted twice with ether
  4. temperaturecooled in an ice-water bath
  5. extractionthe product extracted into ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo to a gummy solid which
  10. customwas crystallized by trituration with hexane
  11. filtrationrecovered by filtration (1.34 g., m.p. 156°-159° C.)
  12. customRecrystallization from chloroform
  13. customgave
  14. custompurified 5-(3,4-dichlorophenylthio)pyrrole-3-carboxylic acid (850 mg., m.p. 159°-161° C.)

出典と根拠

ORDレコード
ord-bb5635b5e3fb43ad983af356ec569c5b
出典データセット
uspto-grants-1981_08
特許番号
US04282242

反応ノート

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