Methanimidamide, hydrochloride (1:1) → 6,7-Dihydro-7-(4-nitrobenzoyl)-5H-pyrimido[5,4-d][1]benzazepine

HRID 1288932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1288932
Cl.[CH:2]([NH2:4])=[NH:3].C[O-].[Na+].CN([CH:11]=[C:12]1[C:18](=O)[C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[N:15]([C:24](=[O:34])[C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=2)[CH2:14][CH2:13]1)C>CO>[N+:31]([C:28]1[CH:29]=[CH:30][C:25]([C:24]([N:15]2[C:16]3[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=3[C:18]3[N:3]=[CH:2][N:4]=[CH:11][C:12]=3[CH2:13][CH2:14]2)=[O:34])=[CH:26][CH:27]=1)([O-:33])=[O:32]

Komponenten

5

Edukt 3

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 10942334Sodium MethoxideHCID 536535644-[(dimethylamino)methylene]-1,2,3,4-tetrahydro-1-(4-nitrobenzoyl)-5H-1-benzazepin-5-one

Produkt 1

HCID 545281396,7-Dihydro-7-(4-nitrobenzoyl)-5H-pyrimido[5,4-d][1]benzazepineAusbeute 107,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of 0.152 g (1.89 mmol) of formamidine hydrochloride in 10 ml of methanol under argon is added 0.102 g (1.89 mmol) of sodium methoxide. After stirring 5 min., a solution of 0.46 g (1.26 mmol) of 4-[(dimethylamino)methylene]-1,2,3,4-tetrahydro-1-(4-nitrobenzoyl)-5H-1-benzazepine-5-one in 5 ml of methanol is added and the mixture stirred 18 hours. The solvent is removed, dichloromethane added, and the mixture filtered. The solid is washed with dichloromethane. The combined filtrate is concentrated to dryness to give 0.47 g of tan foam. The preceding solid is purified by chromatography on silica gel. The compound is dissolved in ethyl acetate-dichloromethane and applied to the column. The column is then eluted with ethyl acetate to give 0.25 g of product as pale yellow crystals.

Aufarbeitung

  1. stirringthe mixture stirred 18 hours
  2. customThe solvent is removed
  3. additiondichloromethane added
  4. filtrationthe mixture filtered
  5. washThe solid is washed with dichloromethane
  6. concentrationThe combined filtrate is concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-92765e261a3345f48df74b15f8c92e35
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05747487

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