1,3-Dichloroacetone → HCID 24772799, Verbindung

HRID 242170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 242170
[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:28]=[N:29][C:30]([NH:33][CH2:34][CH2:35][OH:36])=[CH:31][CH:32]=2)[C:22]([C:37]#[N:38])=[C:21]([SH:39])[N:20]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:18][C:19]1[C:24]([C:25]#[N:26])=[C:23]([C:27]2[CH:28]=[N:29][C:30]([NH:33][CH2:34][CH2:35][OH:36])=[CH:31][CH:32]=2)[C:22]([C:37]#[N:38])=[C:21]([S:39][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 178510479HCID 178510479, Verbindung

Produkt 1

HCID 24772799HCID 24772799, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

18 mg (0.10 mmol) of 4-fluorophenylthiourea and 13 mg (0.10 mmol) of 1,3-dichloroacetone are dissolved in 2 ml of DMF, and the reaction solution is stirred at 80° C. for 3 h. After cooling, 89 mg (0.09 mmol, 33% pure) of the compound from example 4A and 32 mg (0.38 mmol) of sodium bicarbonate are added, and the mixture is stirred at RT for a further 20 h. The mixture is then filtered through a paper filter, and the filtrate is purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). Sat. sodium bicarbonate solution (5 ml) is added to the product fraction obtained, and the mixture is extracted with ethyl acetate (three times, 5 ml each). The combined organic phases are dried over magnesium sulphate, and the solvent is removed on a rotary evaporator.

Aufarbeitung

  1. temperatureAfter cooling
  2. stirringthe mixture is stirred at RT for a further 20 h
  3. filtrationThe mixture is then filtered through a paper
  4. filtrationfilter
  5. customthe filtrate is purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)
  6. additionSat. sodium bicarbonate solution (5 ml) is added to the product fraction
  7. customobtained
  8. extractionthe mixture is extracted with ethyl acetate (three times, 5 ml each)
  9. dry with materialThe combined organic phases are dried over magnesium sulphate
  10. customthe solvent is removed on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-96773f5eb4fe4badb83c976954de3863
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653109B2

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