Acetamidine monohydrochloride → 6,7-dihydro-2-methyl-7-(4-nitrobenzoyl)-5H-pyrimido[5,4-d][l]benzazepine

HRID 362363

Reaktionsgleichung

Reaktionsgleichung von HRID 362363
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].O(C)[Na].CN([CH:12]=[C:13]1[C:19](=O)[C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[N:16]([C:25](=[O:35])[C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)[CH2:15][CH2:14]1)C>CO>[CH3:3][C:2]1[N:4]=[CH:12][C:13]2[CH2:14][CH2:15][N:16]([C:25](=[O:35])[C:26]3[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=3)[C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[C:19]=2[N:5]=1

Komponenten

5

Edukt 3

HCID 67170Acetamidine monohydrochlorideHCID 536535644-[(dimethylamino)methylene]-1,2,3,4-tetrahydro-1-(4-nitrobenzoyl)-5H-1-benzazepin-5-oneHCID 178418582HCID 178418582, Verbindung

Produkt 1

HCID 543797936,7-dihydro-2-methyl-7-(4-nitrobenzoyl)-5H-pyrimido[5,4-d][l]benzazepineAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 0.233 g of acetamidine hydrochloride in 36 ml of methyl alcohol under argon is added 0.133 g of NaOCH3. After 5 minutes, 0.600 g of 4-[(dimethylamino)methylene]-1,2,3,4-tetrahydro-1-(4-nitrobenzoyl)-5H-1-benzazepin-5-one is added and stirring continued for 18 hours. The volatiles are evaporated to a residue which is dissolved in ethyl acetate and passed through a pad of silica gel. The filtrate is evaporated in vacuo to give 590 mg of the desired product as tan crystals, m.p. 211°-212° C. HR FABMS: Exact mass (M+H):361.1295.

Aufarbeitung

  1. waitcontinued for 18 hours
  2. customThe volatiles are evaporated to a residue which
  3. dissolutionis dissolved in ethyl acetate
  4. customThe filtrate is evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a0fa1fe4d0924359a6a946b2649fe97b
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869483

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