Ethyl chloroformate → HCID 21316844, Verbindung

HRID 263268

Reaktionsgleichung

Reaktionsgleichung von HRID 263268
[CH3:1][C:2]([CH3:8])([CH2:6][CH3:7])C(O)=O.ClC([O:12][CH2:13]C)=O.[N-:15]=[N+]=[N-].[Na+].[NH2:19][CH:20]([CH3:23])[C:21]#[N:22]>O.C(N(CC)CC)C.CC(C)=O>[C:21]([CH:20]([NH:19][C:13]([NH:15][C:2]([CH3:1])([CH3:8])[CH2:6][CH3:7])=[O:12])[CH3:23])#[N:22]

Komponenten

8

Edukt 4

HCID 10928Ethyl chloroformateHCID 116842,2-Dimethylbutanoic acidHCID 33557Sodium AzideHCID 411840Propanenitrile, 2-amino-

Produkt 1

HCID 21316844HCID 21316844, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a stirring solution of 23.5 g (0.2 mole) 2,2-dimethylbutanoic acid in 150 ml. acetone, there is added 30 ml. triethylamine. The temperature is lowered to 0°, and 21.1 ml. (0.22 mol) ethyl chloroformate are added over one-half hour, keeping the temperature at 0°. At the end of the addition, the mixture is stirred for 15 minutes, keeping the temperature at 0°. At the end of this period, a solution of 26.0 g. (0.4 mole) sodium azide in 75 ml. of water is added over one-half hour, keeping the temperature at 0°. The resulting mixture is stirred one hour at 0°. At the end of this period, the mixture is poured into 750 ml. of ice water. This mixture is extracted 4 times with 200 ml. toluene. The toluene portions are combined and dried. The toluene solution is added dropwise to 150 ml. of toluene refluxing in a nitrogen atmosphere. After the addition is complete, the solution is heated to reflux until the IR shows the disappearance of the azide peak (about two and one-half hours). The solution is then cooled and 14.0 g. (0.2 mole) 2-aminopropionitrile are added. The resulting mixture is refluxed for 5 hours. At the end of this period, the toluene is removed at reduced pressure. The residue is put through a column of Silica AR CC7 using toluene:ethyl acetate, 80:20 as the liquid phase. The desired portions are combined and the toluene and ethyl acetate are removed under reduced pressure. The residue is recrystallized from ethyl acetate/cyclohexane to give the product, N-(1-cyanoethyl)-N'-(1,1-dimethylpropyl)urea, m.p. 129°-30°. Anal. Calcd. for C8H17N3O: C: 58.99, H: 9.35, N: 22.93; Found: C: 58.82, H: 9.13, N: 22.92.

Aufarbeitung

  1. customis lowered to 0°
  2. customat 0°
  3. additionAt the end of the addition
  4. customat 0°
  5. customat 0°
  6. stirringThe resulting mixture is stirred one hour at 0°
  7. additionAt the end of this period, the mixture is poured into 750 ml
  8. extractionThis mixture is extracted 4 times with 200 ml
  9. customdried
  10. additionThe toluene solution is added dropwise to 150 ml
  11. additionAfter the addition
  12. temperaturethe solution is heated
  13. temperatureto reflux until the IR
  14. temperatureThe solution is then cooled
  15. temperatureThe resulting mixture is refluxed for 5 hours
  16. customAt the end of this period, the toluene is removed at reduced pressure
  17. customthe toluene and ethyl acetate are removed under reduced pressure
  18. customThe residue is recrystallized from ethyl acetate/cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-b3787eb71c934dd7b64be2e21d520af9
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04156738

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