Carbamate → HCID 178467450, Verbindung

HRID 2082643

Reaktionsgleichung

Reaktionsgleichung von HRID 2082643
[CH2:1]([O:3][C:4]([NH:6][C:7](=[O:11])OCC)=S)[CH3:2].C(=O)([O-])[O-].[K+].[K+].ClC1N=C(OCC)[N:22]=[C:21]([N:28]([CH3:30])[CH3:29])[N:20]=1.[Na].C(=O)([O-])N.ClC1N=C(Cl)N=C(N(C)C)N=1>O.C(O)C>[CH3:29][N:28]([CH3:30])[C:21]1[N:22]=[C:4]([O:3][CH2:1][CH3:2])[NH:6][C:7](=[O:11])[N:20]=1

Komponenten

9

Edukt 6

HCID 276CarbamateHCID 11430Potassium CarbonateHCID 169852,4-Dichloro-6-(dimethylamino)-1,3,5-triazineHCID 3457746Ethyl ethoxythiocarbonylcarbamateHCID 5360545SodiumHCID 23338142HCID 23338142, Verbindung

Produkt 1

HCID 178467450HCID 178467450, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

Ethyl ethoxythiocarbonylcarbamate (1 molar proportion) was added to a stirred solution of potassium carbonate in water (10 ml. per gram of carbamate). After 15 minutes stirring, the solution was filtered and dimethyl sulphate added dropwise to the filtrate with vigorous stirring over 45 minutes. The mixture was then stirred for 1 hour and extracted with light petroleum. The extracts were dried and cooled to -40° C., when the carbamate separated. Recrystallised from petroleum, the carbamate had a melting point of 38°-39° C. (b) N,N-Dimethylguanidine hydrochloride (3.23 g; 0.026 mol.) was added to a solution of sodium (0.61 g; 0.026 mol.) in anhydrous ethanol (50 ml.) and the mixture was heated under reflux for 30 minutes. The carbamate prepared in (a) above (5.0 g., 0.026 mol.) was then added and the mixture heated under reflux for 22 hours. The ethanol was removed, water (75 ml.) added, and the pH of the solution adjusted to 6 to 7 with acetic acid. The product was collected, washed with water, and recrystallised from ethanol to give 4-dimethylamino-6-ethoxy-1,3,5-triazin-2-one.

Aufarbeitung

  1. filtrationthe solution was filtered
  2. additiondimethyl sulphate added dropwise to the filtrate
  3. stirringwith vigorous stirring over 45 minutes
  4. stirringThe mixture was then stirred for 1 hour
  5. extractionextracted with light petroleum
  6. customThe extracts were dried
  7. customwhen the carbamate separated
  8. customRecrystallised from petroleum
  9. temperaturethe mixture was heated
  10. temperatureunder reflux for 30 minutes
  11. additionwas then added
  12. temperaturethe mixture heated
  13. temperatureunder reflux for 22 hours
  14. customThe ethanol was removed
  15. additionwater (75 ml.) added
  16. customThe product was collected
  17. washwashed with water
  18. customrecrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-67e8774646044b929977253ff5a2ce63
Quelldatensatz
uspto-grants-1978_04
Patentnummer
US04082536

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