Isobutylamine → 5-[4-(isobutylamino)-3-nitrophenyl]-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one

HRID 1517180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517180
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]([CH3:14])[S:12][C:11](=[O:15])[NH:10][N:9]=2)=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[CH2:19]([NH2:23])[CH:20]([CH3:22])[CH3:21]>C(#N)C>[CH2:19]([NH:23][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]([CH3:14])[S:12][C:11](=[O:15])[NH:10][N:9]=2)=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17])[CH:20]([CH3:22])[CH3:21]

Komponenten

4

Edukt 2

HCID 6558IsobutylamineHCID 148515165-(4-chloro-3-nitrophenyl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one

Produkt 1

HCID 595690275-[4-(isobutylamino)-3-nitrophenyl]-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-oneAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To 15 ml of acetonitrile are added 2.9 g (10.1 mM) of 5-(4-chloro-3-nitrophenyl)-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one and 5 ml (50 mM) of isobutylamine. The reaction medium is maintained at 60° C. for 20 hours with stirring and is then concentrated under vacuum. The residue obtained is purified on silica using dichloromethane as eluent. The product obtained is taken up and crystallised from diethyl ether. The solid is filtered off and washed to give 2.6 g of 5-[4-(isobutylamino)-3-nitrophenyl]-6-methyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one.

Aufarbeitung

  1. concentrationis then concentrated under vacuum
  2. customThe residue obtained
  3. customis purified on silica
  4. customThe product obtained
  5. customcrystallised from diethyl ether
  6. filtrationThe solid is filtered off
  7. washwashed

Quellen und Nachweise

ORD-Eintrag
ord-86c9682da93942358b8cbb823ffad1e3
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232272B2

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