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Hydrochloric Acid → 4-{[(2-{[5-(4-t-Butylphenyl)-4-hydroxy-3-thienyl]methylene}hydrazino)carbonothioyl]amino}benzoic acid

HRID 1881599
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1881599
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14]([CH:17]=O)[C:15]=2[OH:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:19]([C:21]([NH:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1)=[S:22])[NH2:20].Cl>CN(C)C=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[S:12][CH:13]=[C:14]([CH:17]=[N:20][NH:19][C:21]([NH:23][C:24]3[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=3)=[S:22])[C:15]=2[OH:16])=[CH:9][CH:10]=1)([CH3:2])([CH3:3])[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 27573784-(4-Carboxyphenyl)-3-thiosemicarbazideHCID 860145662-(4-t-Butylphenyl)-3-hydroxy-4-formylthiophene

Produkt 1

HCID 723600074-{[(2-{[5-(4-t-Butylphenyl)-4-hydroxy-3-thienyl]methylene}hydrazino)carbonothioyl]amino}benzoic acidAusbeute 23,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

2-(4-t-Butylphenyl)-3-hydroxy-4-formylthiophene (50 mg, 0.19 mmol) synthesized in Reference Synthetic Example 25 and 4-hydrazinocarbonothioylaminobenzoic acid (40 mg, 0.19 mmol) were stirred with dimethylformamide (1.9 mL) and concentrated hydrochloric acid (0.1 mL) at room temperature for 12 hours. The reaction solution was partitioned between ethyl acetate and water, and the organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The resulting organic layer was concentrated and purified by silica gel column chromatography (chloroform). Methanol/chloroform was added to the resulting crude product, and the precipitated yellow solid was recovered by filtration to give the desired product as a pale yellow solid (20 mg, yield 23%).

Aufarbeitung

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe resulting organic layer was concentrated
  5. custompurified by silica gel column chromatography (chloroform)
  6. additionMethanol/chloroform was added to the resulting crude product
  7. filtrationthe precipitated yellow solid was recovered by filtration

Quellen und Nachweise

ORD-Eintrag
ord-42dffd5bd13d43eeb2eb4d56821e0468
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08318796B2

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