Ammonium Chloride → HCID 178439104, Verbindung

HRID 877374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877374
[C:1]([CH:3]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:4][C:5](=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=1)#[N:2].[NH4+].[Cl-].[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C>[CH:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C:5]([NH:4][CH:3]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:1]2[NH:27][N:26]=[N:25][N:2]=2)=[O:16])=[CH:8][CH:9]=1)([CH3:15])[CH3:14]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 67165955HCID 67165955, Verbindung

Produkt 1

HCID 178439104HCID 178439104, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution N-[cyano(phenyl)methyl]-2-(4-isopropylphenyl)acetamide (58.0 mg, 0.198 mmol) in 0.5 ml of anhydrous DMF was added NH4Cl (12.0 mg, 0.218 mmol) and NaN3 (14.00 mg, 0.218 mmol). The resulting solution was stirred at 110° C. for 16 hour. Filtered and the filtrate was purified by preparative HPLC (5-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column) to afford 53.0 mg (80%) of the title compound. 1H NMR (CD3OD, 400 MHz) δ 7.326 (m, 5H), 7.169 (ABq, J=8.2 Hz, 4H), 6.460 (s, 1H), 3.583 (ABq, J=14.5 Hz, 2H), 2.856 (sept, J=7.0 Hz, 1H), 1.214 (d, J=7.0 Hz, 6H). ES-MS [M+1]+: 336.2.

Aufarbeitung

  1. filtrationFiltered
  2. customthe filtrate was purified by preparative HPLC (5-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column)

Quellen und Nachweise

ORD-Eintrag
ord-19928c21c6ce4c04b5b68efd1d0af8d7
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987310B2

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