Methylamine → 5-(1H-indol-5-yl)-N-methyl-1,3,4-thiadiazol-2-amine

HRID 634151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 634151
CS([C:5]1[S:9][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15](C([O-])=O)[CH:14]=[CH:13]3)=[N:7][N:6]=1)(=O)=O.[CH3:22][NH2:23].CCOC(C)=O>CS(C)=O>[NH:15]1[C:16]2[C:12](=[CH:11][C:10]([C:8]3[S:9][C:5]([NH:23][CH3:22])=[N:6][N:7]=3)=[CH:18][CH:17]=2)[CH:13]=[CH:14]1

Komponenten

5

Edukt 3

HCID 6329MethylamineHCID 8857Ethyl AcetateHCID 867250995-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)-1H-indole-1-carboxylate

Produkt 1

HCID 683279525-(1H-indol-5-yl)-N-methyl-1,3,4-thiadiazol-2-amineAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a mixture of 5-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)-1H-indole-1-carboxylate (8 g, 21.11 mmol) in a sealed tube was added methylamine in DMSO (80 mL). The reaction was heated at 110° C. for 1 h and ice-cold water and EtOAc was added. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 40% EtOAc in Hex) to give 5-(1H-indol-5-yl)-N-methyl-1,3,4-thiadiazol-2-amine (3.8 g, 78%). MS (ESI, pos. ion) m/z: 231 (M+1); 1H-NMR (DMSO-d6, 300 MHz): δ ppm 2.9 (s, 3H), 6.5 (d, 1H) 7.4 (d, 3H) 7.8 (m, 1H), 7.9 (s, 1H), 11.4 (s, 1H).

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel chromatography (eluting with 40% EtOAc in Hex)

Quellen und Nachweise

ORD-Eintrag
ord-d3197d52fd7a46fdbf573e6ad9d5ebbe
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321756B2

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