Water → 7-Nitro-1,2,4,5-tetrahydro-benzo(e)(1,3)diazepin-3-one

HRID 1040724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1040724
[NH2:1][CH2:2][C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].C1N=CN([C:19](N2C=NC=C2)=[O:20])C=1.O>O1CCCC1>[N+:11]([C:9]1[CH:8]=[CH:7][C:4]2[CH2:5][NH:6][C:19](=[O:20])[NH:1][CH2:2][C:3]=2[CH:10]=1)([O-:13])=[O:12]

Komponenten

5

Edukt 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 224518872-Aminomethyl-4-nitrobenzylamine

Produkt 1

HCID 105125087-Nitro-1,2,4,5-tetrahydro-benzo(e)(1,3)diazepin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2-aminomethyl-4-nitrobenzylamine (3.10 g, 17.1 mmol) was dissolved in tetrahydrofuran (300 mL) and a solution of N,N-carbonyldiimidazole (2.78 g, 17.1 mmol) in THF (40 mL) was added dropwise at room temperature over 30 minutes. The reaction was allowed to stir at room temperature for 72 hours. The solution was then poured over water (150 mL) and organics were extracted with ethyl acetate (3×100 mL). Combined organic extracts were dried over Na2SO4, filtered and reduced to afford 7-nitro-1,2,4,5-tetrahydro-benzo(e)(1,3)diazepin-3-one as a crude brown solid. Purification by flash column chromatography (0% MeOH/DCM-10% MeOH/DCM) afforded 2.5 grams of 7-nitro-1,2,4,5-tetrahydro-benzo(e)(1,3)diazepin-3-one as a yellow solid. LC/MS (ESI)=208.42 (M+H).

Aufarbeitung

  1. extractionorganics were extracted with ethyl acetate (3×100 mL)
  2. dry with materialCombined organic extracts were dried over Na2SO4
  3. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-72684f3825e545929517cf2aa97373cd
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552186B2

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