Nitromethane → 7-Chloro-1,3-dihydro-2-nitromethylene-5-phenyl-2H-1,4-benzodiazepine

HRID 649263

Reaktionsgleichung

Reaktionsgleichung von HRID 649263
[N+:1]([CH3:4])([O-:3])=[O:2].[H-].[Na+].[H-].[Cl:8][C:9]1[CH:10]=[CH:11][C:12]2[N:18]=[C:17](OP(N3CCOCC3)(N3CCOCC3)=O)[CH2:16][N:15]=[C:14]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:13]=2[CH:40]=1>CN(C)C=O>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]2[NH:18][C:17](=[CH:4][N+:1]([O-:3])=[O:2])[CH2:16][N:15]=[C:14]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:13]=2[CH:40]=1

Komponenten

6

Edukt 4

HCID 6375NitromethaneHCID 24758Sodium hydrideHCID 166653HydrideHCID 149078867-chloro-2-di-(morpholino)phosphinyloxy-5-phenyl-3H-1,4-benzodiazepin

Produkt 1

HCID 700537327-Chloro-1,3-dihydro-2-nitromethylene-5-phenyl-2H-1,4-benzodiazepine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 1.0 ml. of nitromethane and 5 ml. of dry dimethylformamide was added 53 mg. of a 50% dispersion of sodium hydride in mineral oil (1.1 mmole hydride). After 1 hour at room temperature, under nitrogen, 489 mg. (1.0 mmole) of 7-chloro-2-di-(morpholino)phosphinyloxy-5-phenyl-3H-1,4-benzodiazepine was added. After stirring at room temperature for 2 hours, dimethylformamide was evaporated (about 80°). The residue was partitioned between methylene chloride and an aqueous layer which is acidified with a slight excess of acetic acid. The methylene chloride layer was dried (Na2SO4) and evaporated. Separation of the product mixture by preparative tlc (silica gel, developed in 10% methanol in ethylacetate v/v) afforded pure final product, which upon crystallization from methanol, had a m.p. of 178°-180°.

Aufarbeitung

  1. additionTo a mixture of 1.0 ml
  2. customdimethylformamide was evaporated (about 80°)
  3. customThe residue was partitioned between methylene chloride
  4. dry with materialThe methylene chloride layer was dried (Na2SO4)
  5. customevaporated
  6. customSeparation of the product mixture by preparative tlc (silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e23de29fe43843a3aa50a16921825b2f
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04739049

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