Formaldehyde → Ro 14-7437

HRID 67319

Reaktionsgleichung

Reaktionsgleichung von HRID 67319
[NH2:1][C:2](=[C:8]1[CH2:14][N:13]([CH3:15])[C:12](=[O:16])[C:11]2[CH:17]=[CH:18][CH:19]=[CH:20][C:10]=2[NH:9]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:21]=O>C(Cl)Cl>[CH3:15][N:13]1[C:12](=[O:16])[C:11]2[CH:17]=[CH:18][CH:19]=[CH:20][C:10]=2[N:9]2[CH:21]=[N:1][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]2[CH2:14]1

Komponenten

4

Edukt 2

HCID 712FormaldehydeHCID 70541641ethyl alpha-amino-1,3,4,5-tetrahydro-4-methyl-5-oxo-2H-1,4-benzodiazepin-2-ylidene-acetate

Produkt 1

HCID 127597Ro 14-7437

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.0 g of ethyl α-amino-1,3,4,5-tetrahydro-4-methyl-5-oxo-2H-1,4-benzodiazepin-2-ylidene-acetate are dissolved in 20 ml of methylene chloride, treated with 0.65 ml of 37 percent aqueous formaldehyde solution and stirred in the presence of air at room temperature for 2 hours. The solution is subsequently washed twice with 10 ml of water each time. The organic phase is separated, dried and decolourised with active carbon. After filtration of the carbon, the filtrate is evaporated in vacuo and the residue is chromatographed on 20 g of silica gel. Elution is carried out firstly with chloroform and subsequently with chloroform/ethanol (985:15). The fractions which contain ethyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate as the main component are combined and evaporated in vacuo. The residue is dissolved in ethanol and crystallised by the addition of diisopropyl ether. There is obtained ethyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate of melting point 162°-164° C.

Aufarbeitung

  1. washThe solution is subsequently washed twice with 10 ml of water each time
  2. customThe organic phase is separated
  3. customdried
  4. filtrationAfter filtration of the carbon
  5. customthe filtrate is evaporated in vacuo
  6. customthe residue is chromatographed on 20 g of silica gel
  7. washElution
  8. customevaporated in vacuo
  9. dissolutionThe residue is dissolved in ethanol
  10. customcrystallised by the addition of diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-34ed473f514a4ad88b0777a86c397cc9
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04346030

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