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Dimethylamine → 2-(4-Tert-butyl-benzenesulfonylamino)-5-chlorobenzoyl chloride

HRID 1692124
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1692124
S(Cl)([Cl:3])=O.[C:5]([C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:27]=[C:26](F)[C:25]([Cl:29])=[CH:24][C:20]=2[C:21]([OH:23])=O)(=[O:17])=[O:16])=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6].CNC.C[N-]C>C1COCC1.CCCCCC>[C:5]([C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:27]=[CH:26][C:25]([Cl:29])=[CH:24][C:20]=2[C:21]([Cl:3])=[O:23])(=[O:17])=[O:16])=[CH:11][CH:10]=1)([CH3:7])([CH3:8])[CH3:6]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 674DimethylamineHCID 24386Thionyl ChlorideHCID 182180DimethylazanideHCID 593030312-(4-Tert-butyl-benzenesulfonylamino)-5-chloro-4-fluoro-benzoic acid

Produkt 1

HCID 866183462-(4-Tert-butyl-benzenesulfonylamino)-5-chlorobenzoyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Thionyl chloride (220 mL, 3.02 mol) was introduced to a 1 L round bottom flask fitted with a magnetic stir bar. 2-(4-tert-Butyl-benzenesulfonylamino)-5-chloro-4-fluoro-benzoic acid (22 g, 57.0 mmol) was added under rapid agitation and the mixture was heated at reflux under a nitrogen atmosphere. The reaction progress was monitored by the addition of a few drops of the reaction mixture into ˜1 mL of 2.0 M dimethylamine in THF, followed by LCMS analysis. Complete conversion to the dimethyl amide was observed at 1.25 h. The crude mixture was subsequently concentrated in vacuo to produce an orange oil. Hexane (50 mL) was added to the flask and the mixture concentrated again to afford 2-(4-tert-butyl-benzenesulfonylamino)-5-chloro-benzoyl chloride as an orange crystalline solid which was utilized direction in the next step.

Aufarbeitung

  1. customfitted with a magnetic stir bar
  2. temperaturethe mixture was heated
  3. temperatureat reflux under a nitrogen atmosphere
  4. concentrationThe crude mixture was subsequently concentrated in vacuo
  5. customto produce an orange oil
  6. concentrationthe mixture concentrated again

Quellen und Nachweise

ORD-Eintrag
ord-46938bff222743bab672f7dfbb2f4636
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08153818B2

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