Triethylamine → HCID 42633472, Verbindung

HRID 1009042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009042
[CH3:1][C:2]1[CH:6]=[C:5]([S:7](=[O:10])(=[O:9])[NH2:8])[S:4][C:3]=1[CH2:11][CH2:12][O:13][C:14](=[O:16])[CH3:15].Cl[C:18](OC1C=CC=CC=1)=[O:19].C(N(CC)CC)C.[Br:34][C:35]1[S:39][C:38]([NH2:40])=[N:37][C:36]=1[CH3:41]>C(#N)C>[C:14]([O:13][CH2:12][CH2:11][C:3]1[S:4][C:5]([S:7]([NH:8][C:18](=[O:19])[NH:40][C:38]2[S:39][C:35]([Br:34])=[C:36]([CH3:41])[N:37]=2)(=[O:10])=[O:9])=[CH:6][C:2]=1[CH3:1])(=[O:16])[CH3:15]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 129543735-Bromo-4-methyl-1,3-thiazol-2-amineHCID 67273589HCID 67273589, Verbindung

Produkt 1

HCID 42633472HCID 42633472, VerbindungAusbeute 50,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Acetic acid 2-(3-methyl-5-sulfamoyl-thiophen-2-yl)-ethyl ester (0.120 g, 0.456 mmol) was dissolved in 4.5 mL of abs. acetonitrile and treated successively with phenyl chloroformate (0.057 g, 1.00 eq.) and triethylamine (0.159 mL, 2.5 eq.), and the mixture kept at ambient temperature for 1 h. 5-Bromo-4-methyl-thiazol-2-ylamine (0.088 g, 1.00 eq.), dissolved in a tiny amount of acetonitrile, was then added, and the mixture heated to 60° C. over night. Cooling, pouring onto crashed ice/NH4Cl, twofold extraction with ethyl acetate, washing with brine, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, ethyl acetate/5% MeOH), followed by crystallization from ethyl acetate/heptane, yielded finally 0.089 g of the title compound as light brown solid.

Aufarbeitung

  1. additionwas then added
  2. temperatureCooling
  3. additionpouring
  4. extractionice/NH4Cl, twofold extraction with ethyl acetate
  5. washwashing with brine
  6. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  7. customfollowed by crystallization from ethyl acetate/heptane

Quellen und Nachweise

ORD-Eintrag
ord-8f8c23eb95994c4d97d81d5ba567246f
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973051B2

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