StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Triethylamine → N-[(5-bromo-4-ethyl-1,3-thiazol-2-yl)carbamoyl]-5-methylthiophene-3-sulfonamide

HRID 1009027
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1009027
[CH3:1][C:2]1[S:6][CH:5]=[C:4]([S:7]([NH2:10])(=[O:9])=[O:8])[CH:3]=1.Cl[C:12](OC1C=CC=CC=1)=[O:13].C(N(CC)CC)C.[Br:28][C:29]1[S:33][C:32]([NH2:34])=[N:31][C:30]=1[CH2:35][CH3:36]>C(#N)C>[Br:28][C:29]1[S:33][C:32]([NH:34][C:12]([NH:10][S:7]([C:4]2[CH:3]=[C:2]([CH3:1])[S:6][CH:5]=2)(=[O:9])=[O:8])=[O:13])=[N:31][C:30]=1[CH2:35][CH3:36]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 572350435-Methylthiophene-3-sulfonamideHCID 665201935-Bromo-4-ethylthiazol-2-amine

Produkt 1

HCID 42633277N-[(5-bromo-4-ethyl-1,3-thiazol-2-yl)carbamoyl]-5-methylthiophene-3-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
57.5 °C

Versuchsvorschrift

5-Methyl-thiophene-3-sulfonic acid amide (0.0496 g, 0.28 mmol) was dissolved in 1.5 mL of abs. acetonitrile and treated successively with phenyl chloroformate (0.0443 g, 1.01 eq.) and triethylamine (0.097 mL, 2.5 eq.), and the mixture kept at ambient temperature for 1.25 h. The above prepared 5-bromo-4-ethyl-thiazol-2-ylamine (0.061 g, 1.05 eq.), dissolved in a tiny amount of acetonitrile, was then added, and the mixture heated to 55-60° C. over night. Cooling, pouring onto crashed ice/NH4Cl, twofold extraction with ethyl acetate, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, MeOH/ethyl acetate=1/99), yielded eventually, after precipitation from ethyl acetate/heptane, 0.038 g of the title compound as off-white solid.

Aufarbeitung

  1. additionwas then added
  2. temperatureCooling
  3. additionpouring
  4. extractionice/NH4Cl, twofold extraction with ethyl acetate
  5. washwashing with water
  6. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  7. customyielded eventually
  8. customafter precipitation from ethyl acetate/heptane, 0.038 g of the title compound as off-white solid

Quellen und Nachweise

ORD-Eintrag
ord-eb8ee93d08944e4b9b6115fc7395764f
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07973051B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion