Benzene → thietan-3-yl 2-chloro-5-[3,6-dihydro-2 6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoate

HRID 2165796Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2165796
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]2=[O:24])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[S:25](Cl)(Cl)=O.[CH:29]1[CH:34]=CC=C[CH:30]=1>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:21])([F:20])[F:22])[N:14]([CH3:23])[C:13]2=[O:24])=[CH:7][C:3]=1[C:4]([O:6][CH:29]1[CH2:34][S:25][CH2:30]1)=[O:5]

Komponenten

5

Edukt 3

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 120567892-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoic acid

Produkt 1

HCID 23042363thietan-3-yl 2-chloro-5-[3,6-dihydro-2 6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideKatalysator

Versuchsvorschrift

3.0 g of 2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoic acid are heated at reflux temperature for 3 hours in 20 ml of benzene and 2.9 ml of thionyl chloride together with 2 drops of dimethylformamide. The reaction mixture is subsequently evaporated to dryness and dissolved in 20 ml of dioxan. This solution, which consists mainly of the acid chloride of the above-mentioned benzoic acid and the solvent, is added dropwise to a solution of 0.86 g of 3-thietanol and 1.0 g of pyridine in 10 ml of dioxan. The reaction mixture is then stirred at room temperature for 2.5 hours, treated with 400 ml of water and extracted twice with 400 ml of ethyl acetate each time. The combined organic phases are washed twice with 200 ml of 1N hydrochloric acid each time and once with 200 ml of saturated sodium chloride solution, dried over anhydrous sodium sulphate and evaporated. The residue is purified by chromatography on silica gel with ethyl acetate/n-hexane (2:3). In this manner there is obtained thietan-3-yl 2-chloro-5-[3,6-dihydro-2 6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoate which can be recrystallized from ethyl acetate/n-hexane; m.p. 121°-123° C.

Aufarbeitung

  1. customThe reaction mixture is subsequently evaporated to dryness
  2. dissolutiondissolved in 20 ml of dioxan
  3. additionthe solvent, is added dropwise to a solution of 0.86 g of 3-thietanol and 1.0 g of pyridine in 10 ml of dioxan
  4. additiontreated with 400 ml of water
  5. extractionextracted twice with 400 ml of ethyl acetate each time
  6. washThe combined organic phases are washed twice with 200 ml of 1N hydrochloric acid each time
  7. dry with materialonce with 200 ml of saturated sodium chloride solution, dried over anhydrous sodium sulphate
  8. customevaporated
  9. customThe residue is purified by chromatography on silica gel with ethyl acetate/n-hexane (2:3)

Quellen und Nachweise

ORD-Eintrag
ord-a9732dfc9f6f4d8fac8c2d0b8f9a04c6
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04941909

Notizen zur Reaktion

Wird geladen…