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Dicyclohexylcarbodiimide → 3-Methyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dione

HRID 1380419
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1380419
C1CCC(N=C=NC2CCCCC2)CC1.[OH:16][C:17]([CH:19]([C:26]([F:29])([F:28])[F:27])[CH2:20][NH:21][C:22]([NH:24][CH3:25])=[O:23])=O>CN(C=O)C>[CH3:25][N:24]1[C:17](=[O:16])[CH:19]([C:26]([F:29])([F:28])[F:27])[CH2:20][NH:21][C:22]1=[O:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 10868DicyclohexylcarbodiimideHCID 133137911-(2-Hydroxycarbonyl-3,3,3-trifluoropropyl)-3-methylurea

Produkt 1

HCID 130049793-Methyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dioneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of DCC (428 mg; 2.1 mmoles) in DMF (1 ml) was added dropwise to a solution of 1-(2-hydroxycarbonyl-3,3,3-trifluoropropyl)-3-methylurea (428 mg; 2.0 mmoles) obtained above in DMF (2 ml). The mixture was stirred for 1 hour, and the precipitated solid was filtered off and washed with ethyl acetate. The solvents were evaporated under reduced pressure from the combined filtrates. The residue was purified by a column chromatography on silica gel (ethyl acetate:chloroform=1:1) to give 368 mg (yield: 94%) of 3-methyl-5-trifluoromethyl-5,6-dihydrouracil (OF-2).

Aufarbeitung

  1. filtrationthe precipitated solid was filtered off
  2. washwashed with ethyl acetate
  3. customThe solvents were evaporated under reduced pressure from the combined filtrates
  4. customThe residue was purified by a column chromatography on silica gel (ethyl acetate:chloroform=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-bbd2ecfa404748ed8c51d65b861ce89c
Quelldatensatz
uspto-grants-1986_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04581452

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