Acetic acid, 2-isothiocyanato-, ethyl ester → N-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}(thiocarbamoyl)}glycine, ethyl ester

HRID 380789

Reaktionsgleichung

Reaktionsgleichung von HRID 380789
[NH2:1][C:2]1[C:3]([Cl:22])=[CH:4][C:5]([F:21])=[C:6]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]([CH3:19])[C:9]2=[O:20])[CH:7]=1.O1CCCC1.C(O)C.[N:31]([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:32]=[S:33]>C(OCC)(=O)C>[Cl:22][C:3]1[CH:4]=[C:5]([F:21])[C:6]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]([CH3:19])[C:9]2=[O:20])=[CH:7][C:2]=1[NH:1][C:32]([NH:31][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[S:33]

Komponenten

5

Edukt 3

HCID 32202Acetic acid, 2-isothiocyanato-, ethyl esterHCID 186192573-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedioneHCID 21873804Tetrahydrofuran ethanol

Produkt 1

HCID 20695538N-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl}(thiocarbamoyl)}glycine, ethyl esterAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (3.0 g, 8.89 mmol) in a tetrahydrofuran/ethanol solution (1:1) is treated with ethyl isothiocyanatoacetate (1.93 g, 13.34 mmol), refluxed for 9 hours, stirred at room temperature overnight, and concentrated in vacuo to obtain an orange-brown gum. Flash column chromatography of the gum using silica gel and 25% to 30% ethyl acetate in hexanes solutions gives the title product as a white foam (2.24 g, 52% yield, mp 95-103° C.) which is identified by 1H, 13C and 19F NMR spectral analyses.

Aufarbeitung

  1. temperaturerefluxed for 9 hours
  2. concentrationconcentrated in vacuo
  3. customto obtain an orange-brown gum

Quellen und Nachweise

ORD-Eintrag
ord-d408dd087df34ac0b8e5dfe59676176b
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303783B1

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