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Triethylamine → 4-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-trifluoromethyl-benzamide

HRID 2233582
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2233582
[CH2:1]([C:5]1[N:6]=[C:7]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=1)[CH2:2][CH2:3][CH3:4].Cl.[NH2:35][OH:36].C(N(CC)CC)C>O1CCCC1.CO>[CH2:1]([C:5]1[N:6]=[C:7]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]([NH:35][OH:36])=[NH:17])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=1)[CH2:2][CH2:3][CH3:4].[CH2:1]([C:5]1[N:6]=[C:7]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]([NH2:17])=[O:36])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=1)[CH2:2][CH2:3][CH3:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 59296163HCID 59296163, Verbindung

Produkt 2

HCID 866138984-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-trifluoromethyl-benzamideHCID 178441583HCID 178441583, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 180 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-trifluoromethyl-benzonitrile in 5 mL of tetrahydrofuran and 10 ml of methanol was added 267 mg of hydroxylamine hydrochloride followed by 0.55 mL of triethylamine. The resulting mixture was heated to 60° C. overnight. The solvents were removed in vacuo, the resulting residue was poured into water and extracted with ethylacetate. The organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (heptane 1/ethyl acetate 1) to give 90 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-N-hydroxy-2-trifluoromethyl-benzamidine and 50 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-trifluoromethyl-benzamide.

Aufarbeitung

  1. customThe solvents were removed in vacuo
  2. additionthe resulting residue was poured into water
  3. extractionextracted with ethylacetate
  4. dry with materialThe organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel (heptane 1/ethyl acetate 1)

Quellen und Nachweise

ORD-Eintrag
ord-722dc581849240309170170d5d7091d6
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07709509B2

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