Triethylamine → 4-Nitrophenyl 2-cyanoaziridine-1-carboxylate

HRID 378829

Reaktionsgleichung

Reaktionsgleichung von HRID 378829
[C:1]([CH:3]1[CH2:5][NH:4]1)#[N:2].C(N(CC)CC)C.Cl[C:14]([O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:15]>C1COCC1>[C:1]([CH:3]1[CH2:5][N:4]1[C:14]([O:16][C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1)=[O:15])#[N:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 118115Aziridine-2-carbonitrile

Produkt 1

HCID 159175794-Nitrophenyl 2-cyanoaziridine-1-carboxylateAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 175 mg of 2-cyanoaziridine and 0.36 mL of triethylamine in 5 mL of THF was cooled and stirred in an ice bath. A solution of 550 mg of 4-Nitrophenyl chloroformate in 2.5 mL of THF was added at a rate that kept the temperature below 10° C. When the addition was complete, the solution was stirred 2 hours at room temperature and then filtered to remove triethylamine hydrochloride. The filtrate was concentrated under reduced pressure and the residual oil was stirred with 5 mL of toluene for 30 minutes. The pale yellow precipitate that formed was washed with toluene (2×5 mL) and dried under vacuum to afford a 33% yield of 4-nitrophenyl 2-cyanoaziridine-1-carboxylate, m.p. 100-104°C.

Aufarbeitung

  1. customthe temperature below 10° C
  2. additionWhen the addition
  3. stirringthe solution was stirred 2 hours at room temperature
  4. filtrationfiltered
  5. customto remove triethylamine hydrochloride
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. stirringthe residual oil was stirred with 5 mL of toluene for 30 minutes
  8. customThe pale yellow precipitate that formed
  9. washwas washed with toluene (2×5 mL)
  10. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-83fa6475ef5f48f38f2762955ad3012e
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06297230B1

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