Dichloromethane → 5'-Chloro-4-ethoxy-2'-hydroxy-3-thiophenecarboxanilide

HRID 614210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 614210
[CH2:1]([O:3][C:4]1[C:5]([C:9](Cl)=[O:10])=[CH:6][S:7][CH:8]=1)[CH3:2].C(Cl)Cl.[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([OH:23])=[C:20]([CH:22]=1)[NH2:21]>C(N(CC)CC)C>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([OH:23])=[C:20]([CH:22]=1)[NH:21][C:9]([C:5]1[C:4]([O:3][CH2:1][CH3:2])=[CH:8][S:7][CH:6]=1)=[O:10]

Komponenten

5

Edukt 3

HCID 6344Dichloromethane2×HCID 72652-Amino-4-chlorophenolHCID 125737274-Ethoxy-3-thiophenecarbonyl chloride

Produkt 1

HCID 213159805'-Chloro-4-ethoxy-2'-hydroxy-3-thiophenecarboxanilide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

An 8.8 g. portion of 4-ethoxy-3-thiophenecarbonyl chloride is dissolved in 100 ml. of methylene chloride and added dropwise to a mixture of 6.6 g. of 5-chloro-2-hydroxyaniline in 100 ml. of methylene chloride and 6.5 ml. of triethylamine. This mixture is stirred at ambient temperature overnight, concentrated to 100 ml. and filtered. The filtrate is allowed to stand overnight and the precipitate which forms is collected, washed with water and dried in vacuo. This combined precipitate is recrystallized from 200 ml. of ethanol, treated with charcoal, filtered through diatomaceous earth and concentrated giving 5'-chloro-4-ethoxy-2'-hydroxy-3-thiophenecarboxanilide as red brown crystals.

Aufarbeitung

  1. concentrationconcentrated to 100 ml
  2. filtrationand filtered
  3. waitto stand overnight
  4. customthe precipitate which forms is collected
  5. washwashed with water
  6. customdried in vacuo
  7. customThis combined precipitate is recrystallized from 200 ml
  8. additionof ethanol, treated with charcoal
  9. filtrationfiltered through diatomaceous earth
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-862aea1c7d194c82b153557f6da43e53
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04144235

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