Methyl iodide → N-(2-methoxyethyl)-N-methyl-2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide

HRID 1681102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1681102
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][NH:7][S:8]([C:11]1[CH:16]=[C:15]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]2=[O:29])[CH:14]=[CH:13][C:12]=1[Cl:30])(=[O:10])=[O:9].Cl[C:32]1C=CC(N2C(=O)C=C(C(F)(F)F)N(C)C2=O)=CC=1S(Cl)(=O)=O.COCCN.IC>CN(C)C=O>[CH3:3][O:4][CH2:5][CH2:6][N:7]([CH3:32])[S:8]([C:11]1[CH:16]=[C:15]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:25])([F:27])[F:26])[N:19]([CH3:28])[C:18]2=[O:29])[CH:14]=[CH:13][C:12]=1[Cl:30])(=[O:10])=[O:9]

Komponenten

7

Edukt 5

HCID 6328Methyl iodideHCID 80182-MethoxyethylamineHCID 24758Sodium hydrideHCID 153348022-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)pyrimidinyl)benzenesulfonyl chlorideHCID 18993683N-(2-methoxyethyl)-2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide2×

Produkt 1

HCID 18993675N-(2-methoxyethyl)-N-methyl-2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a stirred slurry of 0.2 g of a 60% dispersion of sodium hydride in mineral oil and 30 ml of N,N-dimethylformamide (DMF) cooled to 5° C. was added 1.95 g of N-(2-methoxyethyl)-2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide (Compound #52) prepared according to the procedure set forth above Process B using 2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)pyrimidinyl)benzenesulfonyl chloride and 2-methoxyethylamine. After stirring for 1 hour at 5° C., 0.6 ml of iodomethane was added to the reaction mixture. After stirring at room temperature for 16 hours, the mixture was concentrated using a rotary evaporator. The resulting gummy residue was treated several times with water until a solid had formed. The solid was recrystallized from ethanol to give 1.3 g of the title compound as a whitecrystalline solid, m.p. 108°-110° C. Spectral data for this compound is found in Table I.

Aufarbeitung

  1. customprepared
  2. stirringAfter stirring at room temperature for 16 hours
  3. concentrationthe mixture was concentrated
  4. customa rotary evaporator
  5. additionThe resulting gummy residue was treated several times with water until a solid
  6. customhad formed
  7. customThe solid was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-1950468020934fc5810d7dd86c2b3051
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05169430

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