N,N,N',N'-Tetramethylazodicarboxamide → (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-8-(2-thenyloxy)-1H-1,4-benzodiazepine

HRID 48358

Reaktionsgleichung

Reaktionsgleichung von HRID 48358
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH:6]=[CH:7][C:8]1=[N:9][CH2:10][CH2:11][N:12]([CH3:20])[C:13]2[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:14]1=2.[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[CH2:30]O.C(P(CCCC)CCCC)CCC.N(C(N(C)C)=O)=NC(N(C)C)=O>O1CCCC1>[Cl:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH:6]=[CH:7][C:8]1=[N:9][CH2:10][CH2:11][N:12]([CH3:20])[C:13]2[CH:18]=[C:17]([O:19][CH2:30][C:26]3[S:25][CH:29]=[CH:28][CH:27]=3)[CH:16]=[CH:15][C:14]1=2

Komponenten

6

Edukt 4

HCID 4278N,N,N',N'-Tetramethylazodicarboxamide2×HCID 13831Tributylphosphine2×HCID 694672-ThiophenemethanolHCID 136386027(E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-8-ol hydrochloride

Produkt 1

HCID 69891947(E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-8-(2-thenyloxy)-1H-1,4-benzodiazepineAusbeute 6,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 50 mg (0.14 mmol) of (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-8-ol (prepared as described in Example 157) in 5 ml of dry tetrahydrofuran was added 0.014 ml (0.14 mmol) of thiophene-2-methanol and 0.053 ml (0.21 mmol) of tributylphosphine. The solution was cooled, under an atmosphere of nitrogen, to 0° C. and 37 mg (0.21 mmol) of 1,1′-azobis(N,N-dimethylformamide) was added. The mixture was allowed to warm up to room temperature and then stirred for 16 hours. A further 0.053 ml (0.21 mmol) of tributylphosphine and 37 mg (0.21 mmol) of 1,1′-azobis(N,N-dimethylformamide) were added and the mixture stirred for a further 4 hours. The mixture was filtered and the filtrate evaporated and then chromatographed on silica gel using dichloromethane/methanol (98:2) for the elution. There was obtained 4.2 mg of (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1-methyl-8-(2-thenyloxy)-1H-1,4-benzodiazepine as an orange gum MS: m/e 442.8 [M+H]+.

Aufarbeitung

  1. temperatureto warm up to room temperature
  2. stirringthe mixture stirred for a further 4 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated
  5. customchromatographed on silica gel
  6. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-4eb73e187bc04dcc947e0c7b5301221a
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703387B2

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