3-Nitrophenyl isocyanate → N-[1-(1-Adamantylmethyl)-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]-N'-(3-nitrophenyl)urea

HRID 3081

Reaktionsgleichung

Reaktionsgleichung von HRID 3081
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]=[C:11]=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:13]12([CH2:23][N:24]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[N:28]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:27](=[O:41])[CH:26]([NH2:42])[C:25]3=[O:43])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2>C(#N)C.ClCCl>[C:13]12([CH2:23][N:24]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[N:28]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:27](=[O:41])[CH:26]([NH:42][C:11]([NH:10][C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=4)=[O:12])[C:25]3=[O:43])[CH2:22][CH:17]3[CH2:16][CH:15]([CH2:21][CH:19]([CH2:18]3)[CH2:20]1)[CH2:14]2

Komponenten

5

Edukt 2

HCID 768353-Nitrophenyl isocyanateHCID 109606701-Adamantylmethyl-3-amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Produkt 1

HCID 10793342N-[1-(1-Adamantylmethyl)-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]-N'-(3-nitrophenyl)ureaAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3-nitrophenyl isocyanate (0.082 g) in dry acetonitrile (8 ml) was added to a solution of the 1-(1-Adamantylmethyl-3-amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (0.2 g) in dry acetonitrile (10 ml) under a nitrogen atmosphere. The mixture was stirred at 23° for 2 h, then diluted with dichloromethane (15 ml) and washed with brine (15 ml). The organic solution was dried, concentrated in vacuo and the residue was triturated with diethyl ether to give the title compound as a white solid (0.229 g). M.p. 213°-5°. T.I.c. CH-EA (2:1), Rf0.33.

Aufarbeitung

  1. washwashed with brine (15 ml)
  2. customThe organic solution was dried
  3. concentrationconcentrated in vacuo
  4. customthe residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-854b8b53d833423eaf0208d0354bd8e9
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733867

Verknüpfte Notizen

Wird geladen…