Ethanethiol → Ethiozin

HRID 542924

Reaktionsgleichung

Reaktionsgleichung von HRID 542924
[NH2:1][N:2]1[C:7](=[O:8])[C:6]([C:9]([CH3:12])([CH3:11])[CH3:10])=[N:5][N:4]=[C:3]1[S:13][CH3:14].[CH2:15](S)C.[OH-].[K+]>>[NH2:1][N:2]1[C:7](=[O:8])[C:6]([C:9]([CH3:11])([CH3:10])[CH3:12])=[N:5][N:4]=[C:3]1[S:13][CH2:14][CH3:15]

Komponenten

4

Edukt 3

HCID 6343EthanethiolHCID 14797Potassium HydroxideHCID 30479Metribuzin

Produkt 1

HCID 91689Ethiozin

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A mixture of 230 g (1 mole of 93% active ingredient) of 4-amino-6-t-butyl-3-methylthio-1,2,4-triazin-5-one and 310 g (5 moles) of ethyl mercaptan and 0.5 g of crushed solid KOH was stirred and refluxed onto a 10° C. condenser. The vapors which pass through the condenser (methyl and ethyl mercaptans) were collected in a dry ice or caustic trap. The reaction was continued until thin layer chromotography indicated that the starting material was gone (usually 2-8 hours). The unreacted ethyl mercaptan was then distilled off while ~600 ml of warm (40° C.) water was added at such a rate that the water addition was complete when ~1/3 of the mercaptan had distilled. Distillation was continued until ~100 ml of water distilled at 100° C. The solution was then allowed to cool with rapid stirring. The product crystallized at 60°-70° C. and at 20° C. was filtered and washed with water, then dried. The final product, 4-amino-6-t-butyl-3-ethylthio-1,2,4-triazin-5-one, was obtained in nearly quantitative yield and contained less than 1% of the starting 3-methylthio compound.

Aufarbeitung

  1. customwere collected in a dry ice or caustic trap
  2. customusually 2-8 hours
  3. distillationThe unreacted ethyl mercaptan was then distilled off while ~600 ml
  4. temperatureof warm (40° C.) water
  5. additionwas added at such a rate
  6. additionthat the water addition
  7. distillationhad distilled
  8. distillationDistillation
  9. distillationdistilled at 100° C
  10. temperatureto cool with rapid stirring
  11. customThe product crystallized at 60°-70° C. and at 20° C.
  12. filtrationwas filtered
  13. washwashed with water
  14. customdried

Quellen und Nachweise

ORD-Eintrag
ord-990391ae1aa34f1283e3361081ff929b
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659819

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