Sodium hydride → N,N-dimethyl-2-chloro-5-[3,6-dihydro-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzenesulfonamide

HRID 1681100Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1681100
[H-].[Na+].[NH2:3][C:4]([C:11]([F:14])([F:13])[F:12])=[CH:5][C:6]([O:8]CC)=O.[CH3:15][N:16]([CH3:30])[S:17]([C:20]1[CH:25]=[C:24]([N:26]=[C:27]=[O:28])[CH:23]=[CH:22][C:21]=1[Cl:29])(=[O:19])=[O:18]>O1CCCC1>[CH3:15][N:16]([CH3:30])[S:17]([C:20]1[CH:25]=[C:24]([N:26]2[C:6](=[O:8])[CH:5]=[C:4]([C:11]([F:12])([F:13])[F:14])[NH:3][C:27]2=[O:28])[CH:23]=[CH:22][C:21]=1[Cl:29])(=[O:19])=[O:18]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 136209Ethyl 3-amino-4,4,4-trifluoro-2-butenoateHCID 18993674N,N-dimethyl-2-chloro-5-isocyanatobenzenesulfonamide

Produkt 1

HCID 18993677N,N-dimethyl-2-chloro-5-[3,6-dihydro-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

To 30 ml of dried tetrahydrofuran (THF) cooled to -5° C. was added, under nitrogen, 3.6 g of sodium hydride as a 60% dispersion mineral oil. To the stirred slurry was added a solution of 10 g of ethyl 3-amino-4,4,4-trifluoro-2-butenoate in 30 ml of THF over a period of 30 minutes. After stirring at -5° C. for 1 hour, the reaction mixture was cooled to -65° C. and a solution of N, N-dimethyl-2-chloro-5-isocyanatobenzenesulfonamide (Example A-4 above) in 30 ml of THF was added dropwise maintaining the temperature below -60° C. The mixture was stirred at -65° C. for 2 hours and allowed to warm to room temperature. After stirring for 17 hours, solvent was removed using a rotary evaporator. About 50 ml of water was added to the residue. The resulting mixture was filtered to remove a small amount of undissolved solid and the filtrate was acidified with hydrochloric acid. The resulting precipitate was filtered to give 13 g of the title compound as a beige solid, m.p. 281°-283° C.

Aufarbeitung

  1. additionwas added, under nitrogen
  2. temperaturethe reaction mixture was cooled to -65° C.
  3. temperaturemaintaining the temperature below -60° C
  4. stirringThe mixture was stirred at -65° C. for 2 hours
  5. temperatureto warm to room temperature
  6. stirringAfter stirring for 17 hours
  7. customsolvent was removed
  8. customa rotary evaporator
  9. additionAbout 50 ml of water was added to the residue
  10. filtrationThe resulting mixture was filtered
  11. customto remove a small amount of undissolved solid
  12. filtrationThe resulting precipitate was filtered

Quellen und Nachweise

ORD-Eintrag
ord-8e9516ef5f54497fba2c7bc1b99c3d64
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05169430

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