Water → 5-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]-3,6-dihydro-2H-1,3,4-thiadiazin-2-one

HRID 1517184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517184
Cl.Br[CH2:3][C:4]([C:6]1[CH:26]=[CH:25][C:9]2[N:10]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)=[N:12][C:8]=2[CH:7]=1)=O.N1C=CC=CC=1.[NH:33]([C:35](=[S:39])[O:36]CC)[NH2:34].O>C(O)C>[CH2:21]([N:10]1[C:9]2[CH:25]=[CH:26][C:6]([C:4]3[CH2:3][S:39][C:35](=[O:36])[NH:33][N:34]=3)=[CH:7][C:8]=2[N:12]=[C:11]1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[CH:22]([CH3:24])[CH3:23]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 12567113O-Ethyl hydrazinecarbothioateHCID 866472782-bromo-1-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]ethanone hydrochloride

Produkt 1

HCID 595690375-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]-3,6-dihydro-2H-1,3,4-thiadiazin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 24 g (54.8 mM) of 2-bromo-1-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]ethanone hydrochloride in 500 ml of ethanol are added 6.3 ml (78.4 mM) of pyridine and then 8.2 g (78.4 mM) of O-ethyl hydrazinecarbothioate. The reaction medium is then maintained at 80° C. with stirring for 20 hours. Water is then added and the resulting mixture is extracted with ethyl acetate. The organic phase is washed with water and then dried over anhydrous sodium sulfate and evaporated under vacuum. The residue is purified on a column of silica, using a dichloromethane/methanol mixture (98/2). The residue obtained after evaporation is taken up in diethyl ether to give, after filtration, 10 g of 5-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]-3,6-dihydro-2H-1,3,4-thiadiazin-2-one in the form of a light-beige solid.

Aufarbeitung

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under vacuum
  5. customThe residue is purified on a column of silica
  6. customThe residue obtained
  7. customafter evaporation
  8. customto give
  9. filtrationafter filtration, 10 g of 5-[1-isobutyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]-3,6-dihydro-2H-1,3,4-thiadiazin-2-one in the form of a light-beige solid

Quellen und Nachweise

ORD-Eintrag
ord-66f8c4d56527458cacf56e77140b54b3
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232272B2

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