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1-Butanol → 5-Methyl-2-(2',4'-dichloro-6'-methylanilino)phenylacetic acid

HRID 2087030
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2087030
CN(C)[C:3](=[O:22])[CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[NH:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([Cl:20])=[CH:15][C:14]=1[Cl:21].[OH-].[Na+].CCCC[OH:30].Cl>C1(C)C=CC=CC=1>[CH3:11][C:9]1[CH:8]=[CH:7][C:6]([NH:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([Cl:20])=[CH:15][C:14]=2[Cl:21])=[C:5]([CH2:4][C:3]([OH:22])=[O:30])[CH:10]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15541937N,N-dimethyl-5-methyl-2-(2',4'-dichloro-6'-methylanilino)phenylacetamide

Produkt 1

HCID 98620215-Methyl-2-(2',4'-dichloro-6'-methylanilino)phenylacetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

N,N-dimethyl-5-methyl-2-(2′,4′-dichloro-6′-methylanilino)phenylacetamide (1.5 g, 4.3 mmol) is hydrolyzed with 6N NaOH (70 ml) as a two phase solution with n-BuOH (40 ml) at reflux temperature for 14 hours. After cooling to room temperature, the mixture is poured over ice (100 ml). Toluene (100 ml) is added and the mixture transferred to a separatory funnel. The aqueous phase is brought to a pH of 1 with 3 N HCl. The organic phase is separated and the aqueous phase re-extracted with toluene (100 ml). The combined organic solution is dried (MgSO4) and concentrated under high vacuum (35-50 mbar), on a rotovap, taking care not to warm above 50°. Upon crystallization from Et2O/hexane, 5-methyl-2-(2′,4′-dichloro-6′-methylanilino)phenylacetic acid is obtained as a tan solid, m.p. 137-141°.

Aufarbeitung

  1. temperatureat reflux temperature for 14 hours
  2. customthe mixture transferred to a separatory funnel
  3. customThe organic phase is separated
  4. extractionthe aqueous phase re-extracted with toluene (100 ml)
  5. dry with materialThe combined organic solution is dried (MgSO4)
  6. concentrationconcentrated under high vacuum (35-50 mbar), on a rotovap
  7. temperatureto warm above 50°
  8. customUpon crystallization from Et2O/hexane

Quellen und Nachweise

ORD-Eintrag
ord-e69e3ce2f85a4bbfb6a6779a543c2723
Quelldatensatz
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06727281B2

Notizen zur Reaktion

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