Chlorosuccinimide → HCID 53981427, Verbindung

HRID 442692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 442692
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][C:11](=[O:22])[NH:10][N:9]=2)=[CH:4][CH:3]=1.C1C(=O)N([Cl:30])C(=O)C1>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][C:11](=[O:22])[NH:10][N:9]=2)=[CH:4][C:3]=1[Cl:30]

Komponenten

5

Edukt 2

HCID 31398ChlorosuccinimideHCID 9839097HCID 9839097, Verbindung

Produkt 1

HCID 53981427HCID 53981427, VerbindungAusbeute 47,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-aminophenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4(4H)-one (118 mg, 0.400 mmol) in DMF (3 mL) was added NCS (51 mg, 0.38 mmol). The mixture was stirred at room temperature for 20 h, diluted with EtOAc (50 mL), washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (1:1 hexane/EtOAc) to afford the title compound as a tan solid (60 mg, 0.18 mmol, 45%), mp: 256°-258° C. 1H NMR (CDCl3) 8.50 (s, 1H), 7.54 (s, 1H), 7.32(d, J=8.3, 1H), 6.82 (s, 1H), 6.77 (d, J=8.3, 1H), 6.69 (s, 1H), 6.04 (s, 2H), 4.33 (s, 2H), 3.42 (s, 2H).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography (1:1 hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-80a63c5275104f23839b9382761f4b58
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891871

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