2-Methylamino-5-nitrobenzophenone → Nimetazepam

HRID 1729968

Reaktionsgleichung

Reaktionsgleichung von HRID 1729968
[N:1]([CH2:4][C:5](Cl)=[O:6])=C=O.[CH3:8][NH:9][C:10]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:11]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O>O>[CH3:8][N:9]1[C:10]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:11]=2[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:1][CH2:4][C:5]1=[O:6]

Komponenten

4

Edukt 2

HCID 786612-Methylamino-5-nitrobenzophenoneHCID 132291762-Isocyanatoacetyl chloride

Produkt 1

HCID 4496Nimetazepam

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

2-Milliliters of 2-isocyanatoacetyl chloride was cooled, and 0.20 g. of powdered 2-methylamino-5-nitrobenzophenone was added thereto with stirring. After stirring the resulting mixture at room temperature for one hour, excess 2-isocyanatoacetyl chloride was removed by reduced pressure distillation. To the residue was added 4 ml. of pyridine, whereby a reaction took place with generation of heat. The reaction liquid was heated at 95° C, for 1.5 hours, diluted with water and then extracted with chloroform. The chloroform layer was washed with a 5% aqueous hydrochloric acid solution and then with an aqueous sodium chloride solution in this order, dried over Glauber's salt, and evaporated by reduced pressure distillation. Subsequently, the residue was chromatographically purified (solvent: chloroform→ethyl acetate) by use of a column packed with 10 g. of silica gel to obtain 1-methyl-5-phenyl-7-nitro-1,3-dihydro-2H-1,4-benzodiazepin-2-one having a melting point of 154° to 156° C.

Aufarbeitung

  1. stirringAfter stirring the resulting mixture at room temperature for one hour
  2. customexcess 2-isocyanatoacetyl chloride was removed by reduced pressure distillation
  3. additionTo the residue was added 4 ml
  4. temperatureof heat
  5. customThe reaction liquid
  6. extractionextracted with chloroform
  7. washThe chloroform layer was washed with a 5% aqueous hydrochloric acid solution
  8. dry with materialwith an aqueous sodium chloride solution in this order, dried over Glauber's salt
  9. customevaporated by reduced pressure distillation
  10. customSubsequently, the residue was chromatographically purified (solvent: chloroform→ethyl acetate) by use of a column

Quellen und Nachweise

ORD-Eintrag
ord-442193375f16488eb44e92ef81577abc
Quelldatensatz
uspto-grants-1976_11
Patentnummer
US03991048

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