Pyridine → 2-(3',5'-Dichlorophenyl)-4,4-dimethyl-5-chloro-5-dichloromethyloxazoline

HRID 620930

Reaktionsgleichung

Reaktionsgleichung von HRID 620930
[CH3:1][C:2]([NH:6][C:7](=[O:16])[C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10]([Cl:15])[CH:9]=1)([CH3:5])[C:3]#C.[Cl:17]Cl.N1C=CC=CC=1.[CH2:25]([Cl:27])[Cl:26]>CCOCC>[Cl:15][C:10]1[CH:9]=[C:8]([C:7]2[O:16][C:1]([Cl:17])([CH:25]([Cl:27])[Cl:26])[C:2]([CH3:5])([CH3:3])[N:6]=2)[CH:13]=[C:12]([Cl:14])[CH:11]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 24526ChlorineHCID 32154Propyzamide

Produkt 1

HCID 544601542-(3',5'-Dichlorophenyl)-4,4-dimethyl-5-chloro-5-dichloromethyloxazoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

N-(1',1'-dimethylpropynyl)-3,5-dichlorobenzamide (25 gm, 0.096 m) was dissolved in methylene chloride (300 ml) and excess chlorine (2.5-3 equivalents) was bubbled through this solution at room temperature. After the starting material had disappeared (as indicated by thin layer chromatography, TLC), this solution was washed with aqueous sodium sulfite and the solvent was removed. The white solid obtained was slurried in ether (250 ml) and pyridine (8.0 gm) was added. The mixture was stirred for about 1 hour and then filtered to remove solids. The mother liquor was washed sequentially with cold 1% hydrochloric acid (25 ml), sodium bicarbonate (50 ml), water and brine. The solvent was removed after drying over magnesium sulfate and 28 gm of 2-(3',5'-dichlorophenyl)-4,4-dimethyl-5-chloro-5-dichloromethyloxazoline was obtained.

Aufarbeitung

  1. washthis solution was washed with aqueous sodium sulfite
  2. customthe solvent was removed
  3. customThe white solid obtained
  4. filtrationfiltered
  5. customto remove solids
  6. washThe mother liquor was washed sequentially with cold 1% hydrochloric acid (25 ml), sodium bicarbonate (50 ml), water and brine
  7. customThe solvent was removed
  8. dry with materialafter drying over magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-58ef2b978ca242dbbcb00ae963c4ff57
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04822902

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