Triethylamine → 1-[1-(2-toluoylmethyl)-2-oxo-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-methoxycarbonyl-4-methylphenyl)urea

HRID 1979436Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1979436
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[C:32]1([CH3:62])[C:33]([C:38]([CH2:40][N:41]2[C:47]3[CH:48]=[C:49]([CH3:52])[CH:50]=[CH:51][C:46]=3[N:45]([C:53](=[O:59])[C:54]3[S:58][CH:57]=[CH:56][CH:55]=3)[CH2:44][CH:43]([NH2:60])[C:42]2=[O:61])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1>O1CCCC1.O>[C:32]1([CH3:62])[C:33]([C:38]([CH2:40][N:41]2[C:47]3[CH:48]=[C:49]([CH3:52])[CH:50]=[CH:51][C:46]=3[N:45]([C:53](=[O:59])[C:54]3[S:58][CH:57]=[CH:56][CH:55]=3)[CH2:44][CH:43]([NH:60][C:14]([NH:12][C:9]3[CH:10]=[CH:11][C:2]([CH3:1])=[C:3]([C:4]([O:6][CH3:7])=[O:5])[CH:8]=3)=[O:16])[C:42]2=[O:61])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 15049977Methyl 5-Amino-2-methylbenzoateHCID 212017831-(2-toluoylmethyl)-2-oxo-3-amino-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Produkt 1

HCID 212020311-[1-(2-toluoylmethyl)-2-oxo-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-methoxycarbonyl-4-methylphenyl)ureaAusbeute 252,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Methyl 2-methyl-5-aminobenzoate (0.37 g) was dissolved in tetrahydrofuran (10 ml), triphosgene (0.22 g) was added at internal temperature 5° C., triethylamine (0.95 g) was added thereto over 10 minutes, the mixture was stirred at room temperature for 10 minutes. A solution of 1-(2-toluoylmethyl)-2-oxo-3-amino-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (0.81 g) in tetrahydrofuran (10 ml) was added, the mixture was stirred at room temperature for one hour. Water was added to the reaction mixture, and extracted with chloroform. The organic layer was successively washed with water and saturated brine and dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography(chloroform:methanol=50:1), to thereby obtain 1.17 g of the title compound as light yellow amorphous (Yield: 100%).

Aufarbeitung

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for one hour
  3. extractionextracted with chloroform
  4. washThe organic layer was successively washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography(chloroform:methanol=50:1)

Quellen und Nachweise

ORD-Eintrag
ord-9d597a38403241748585ad8bf55d5730
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06239131B1

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