1,3-Dichloroacetone → HCID 86624334, Verbindung

HRID 2362810

Reaktionsgleichung

Reaktionsgleichung von HRID 2362810
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH2:11])=[S:10])=[CH:4][CH:3]=1.Cl[CH2:13][C:14]([CH2:16]Cl)=O.[NH2:18][C:19]1[C:24]([C:25]#[N:26])=[C:23]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH:35]3[CH2:39][O:38][C:37]([CH3:41])([CH3:40])[O:36]3)=[CH:29][CH:28]=2)[C:22]([C:42]#[N:43])=[C:21]([SH:44])[N:20]=1.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:18][C:19]1[C:24]([C:25]#[N:26])=[C:23]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH:35]3[CH2:39][O:38][C:37]([CH3:40])([CH3:41])[O:36]3)=[CH:29][CH:28]=2)[C:22]([C:42]#[N:43])=[C:21]([S:44][CH2:16][C:14]2[N:11]=[C:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[S:10][CH:13]=2)[N:20]=1

Komponenten

6

Edukt 4

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 6930614-FluorophenylthioureaHCID 178431437HCID 178431437, Verbindung

Produkt 1

HCID 86624334HCID 86624334, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

102 mg (0.6 mmol) of 4-fluorophenylthiourea and 73.6 mg (0.58 mmol) of 1,3-dichloroacetone are dissolved in 2.5 ml of ethanol, and the mixture is stirred under reflux for 60 min. The mixture is allowed to cool and concentrated using a rotary evaporator. The residue is taken up in 1.5 ml of DMF, 153 mg (0.4 mmol) of the compound from Example 3A and 101 mg (1.2 mmol) of sodium bicarbonate are added and the reaction solution is stirred at RT for a further 16 h. The reaction mixture is purified directly by preparative HPLC chromatography (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Aufarbeitung

  1. temperatureunder reflux for 60 min
  2. temperatureto cool
  3. concentrationconcentrated
  4. customa rotary evaporator
  5. stirringthe reaction solution is stirred at RT for a further 16 h
  6. customThe reaction mixture is purified directly by preparative HPLC chromatography (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Quellen und Nachweise

ORD-Eintrag
ord-4e52978ae3a14672b5123e0fbb6a7afb
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691850B2

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