Acetonitrile → Ethyl cyanomethyl(1-(2-nitrophenyl)ethyl)carbamate

HRID 1186108

Reaktionsgleichung

Reaktionsgleichung von HRID 1186108
C(#N)C.[N+:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]([NH:15][CH2:16][C:17]#[N:18])[CH3:14])([O-:6])=[O:5].C([O-])(O)=O.[Na+].Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26]>CCOC(C)=O.C(Cl)Cl>[C:17]([CH2:16][N:15]([CH:13]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[N+:4]([O-:6])=[O:5])[CH3:14])[C:25](=[O:26])[O:27][CH2:28][CH3:29])#[N:18]

Komponenten

7

Edukt 4

HCID 6342AcetonitrileHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 866252282-(1-(2-Nitrophenyl)ethylamino)acetonitrile

Produkt 1

HCID 86625229Ethyl cyanomethyl(1-(2-nitrophenyl)ethyl)carbamateAusbeute 4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Preparation of ethyl cyanomethyl(1-(2-nitrophenylethyl)carbamate (19): To the acetonitrile solution containing 2-(1-(2-nitrophenyl)ethylamino)acetonitrile (18) from the previous step was added saturated NaHCO3 (5 mL) and ethyl chloroformate (1.83 g, 16.86 mmol). The reaction mixture was stirred vigorously at room temperature for 14 hours. The reaction was diluted with EtOAc (50 mL) and washed with brine (40 mL). The separated organic phase was dried over Na2SO4, filtered, and concentrated. Purification (Biotage 40 s, 3:1 CH2Cl2:hexanes, then 100% CH2Cl2) provided 37.1 mg (0.134 mmol, 4% yield) of ethyl cyanomethyl(1-(2-nitrophenyl)ethyl)carbamate (19) as a light yellow oil.

Aufarbeitung

  1. washwashed with brine (40 mL)
  2. dry with materialThe separated organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification (Biotage 40 s, 3:1 CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-adddfb23df0f4c1a882db0c1f4b68a7f
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673898B2

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