Triethylamine → 3,5,5-Trimethyl-2-[[-O-[N-methyl-N-(2-methyl-1,3-dichloro-2-propanesulfenyl)carbamoyl] oximino]]-4-thiazolidinone

HRID 1980107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1980107
[CH3:1][N:2]1[C:6](=[O:7])[C:5]([CH3:9])([CH3:8])[S:4][C:3]1=[N:10][OH:11].[CH3:12][N:13]([S:17][C:18]([CH3:23])([CH2:21][Cl:22])[CH2:19][Cl:20])[C:14](F)=[O:15].C(N(CC)CC)C>O1CCOCC1.O.C(OC(=O)C)C>[CH3:1][N:2]1[C:6](=[O:7])[C:5]([CH3:9])([CH3:8])[S:4][C:3]1=[N:10][O:11][C:14](=[O:15])[N:13]([CH3:12])[S:17][C:18]([CH3:23])([CH2:19][Cl:20])[CH2:21][Cl:22]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 54204012N-Methyl-N-(2-methyl-1,3-dichloro-2-propanesulfenyl)carbamoyl fluorideHCID 713633892-(Hydroxyimino)-3,5,5-trimethyl-1,3-thiazolidin-4-one

Produkt 1

HCID 545396813,5,5-Trimethyl-2-[[-O-[N-methyl-N-(2-methyl-1,3-dichloro-2-propanesulfenyl)carbamoyl] oximino]]-4-thiazolidinoneAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

To a solution of 3.28 g of 3,5,5-trimethyl-2-oximino-4-thiazolidinone and 5.0 g of N-methyl-N-(2-methyl-1,3-dichloro-2-propanesulfenyl)carbamoyl fluoride in 75 ml of dioxane, was added dropwise with stirring 2.18 g of triethylamine. The spontaneous exotherm raised the temperature to 30° C. After following the reaction mixture to stand at room temperature for 16 hours, the reaction mixture was diluted with 300 ml of water. The product was isolated in ethylacetate and purified by column chromatography over silica gel to yield 3.0 g of a white solid. m.p. 91°-92° C.

Aufarbeitung

  1. custompurified by column chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-2a716f53d2524365aced58d636dc940e
Quelldatensatz
uspto-grants-1984_11
Patentnummer
US04485113

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