N,N'-Dimethylthiourea → 2-Methylimino-3-methyl-5-t-butyl-tetrahydro-1,3,5-thiadiazin-4-one

HRID 237073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 237073
[C:1]([N:5]([CH2:9]Cl)[C:6](Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:11][NH:12][C:13]([NH:15][CH3:16])=[S:14]>C1(C)C=CC=CC=1>[CH3:11][N:12]=[C:13]1[N:15]([CH3:16])[C:6](=[O:7])[N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:9][S:14]1

Komponenten

4

Edukt 2

HCID 2723631N,N'-DimethylthioureaHCID 21314703N-t-butyl-N-chloromethylcarbamoyl chloride

Produkt 1

HCID 213147402-Methylimino-3-methyl-5-t-butyl-tetrahydro-1,3,5-thiadiazin-4-oneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

In 50 ml of toluene, were dissolved 3.7 g (0.02 mole) of N-t-butyl-N-chloromethylcarbamoyl chloride and 2.0 g (0.02 mole) of 1,3-dimethylthiourea. The solution was heated under reflux with stirring for one hour. After cooling, the precipitated crystals (m.p. >220° C. decomp.) were collected by filtration, washed with a small quantity of acetone, dissolved again in 100 ml of water, admixed with 10 ml of a 20% sodium hydroxide solution, and extracted with 50 ml of benzene. The benzene layer was dried and concentrated under reduced pressure to obtain 3.5 g (83% yield) of crystals melting at 51°-52° C.

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. filtrationthe precipitated crystals (m.p. >220° C. decomp.) were collected by filtration
  5. washwashed with a small quantity of acetone
  6. dissolutiondissolved again in 100 ml of water
  7. extractionextracted with 50 ml of benzene
  8. dry with materialThe benzene layer was dried
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f1e14114cecc466f8a0db06299925de7
Quelldatensatz
uspto-grants-1979_06
Patentnummer
US04159328

Notizen zur Reaktion

Wird geladen…