Potassium Bromide → 1-(4-Methoxyphenylsulphenyl)methyl-5-chloropyrimidin-2-one

HRID 247075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 247075
Cl.[Cl:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[NH:7][CH:8]=1.Cl[CH2:11][S:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.[K+].[Br-]>CO>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([S:12][CH2:11][N:5]2[CH:4]=[C:3]([Cl:2])[CH:8]=[N:7][C:6]2=[O:9])=[CH:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 253877Potassium BromideHCID 106791911-[(Chloromethyl)sulfanyl]-4-methoxybenzeneHCID 126485235-Chloropyrimidin-2-ol hydrochloride

Produkt 1

HCID 135300981-(4-Methoxyphenylsulphenyl)methyl-5-chloropyrimidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

The title compound was prepared from 5-chloropyrimidin-2-one hydrochloride (10 mmol) and 1-chloromethylthio-4-methoxy benzene [see Preparation 1] (10 mmol) in a manner similar to that described in Example 2. The reaction time was 2 h. Yield: 2.46 g (87%) of the N- and O-isomers in the ratio 7:5. The N-isomer was isolated by its lower solubility in methanol; m.p. 140° C. (MeOH). (Found C41.23; H4.00 Calc. for C12H11ClN2O2S: C50.97; H3.93) 1H NMR (DMSO-d6): δ 3.77 (OMe), 5.12 (CH2), 6.8-7.4 (Ph), 7.90 and 8.56 (H-4 and H-6, respectively, J 4 Hz). IR (KBr): 1660 cm-1 (CO. MS (70 eV, m/z % rel. int.)]: 282/284 (5/2,M), 143/145 (100/33).

Quellen und Nachweise

ORD-Eintrag
ord-6a6a37e1b3954914bcfdb407f8622f7c
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04705791

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