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Dichloromethane → 7-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid isopropyl ester

HRID 1679049
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1679049
C[O-].[Na+].Cl.[CH:5](OC(C1N(CCN(CC)CC)C(C2C=CC=CC=2)=C2C=1C=CC(Cl)=C2)=O)(C)C.C(Cl)Cl.[CH2:37]([O:39][C:40]([CH:42]1[N:48]=[C:47]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:46]2[CH:55]=[C:56]([Cl:59])[CH:57]=[CH:58][C:45]=2[NH:44][C:43]1=[O:60])=[O:41])[CH3:38]>C(O)(=O)C>[CH:37]([O:39][C:40]([CH:42]1[N:48]=[C:47]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:46]2[CH:55]=[C:56]([Cl:59])[CH:57]=[CH:58][C:45]=2[NH:44][C:43]1=[O:60])=[O:41])([CH3:5])[CH3:38]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 110682Ethyl 7-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylateHCID 10942334Sodium MethoxideHCID 706209895-Chloro-2-[2-(diethylamino)ethyl]-3-phenylisoindole-1-carboxylic acid isopropyl ester hydrochloride

Produkt 1

HCID 539649407-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid isopropyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

500 Ml. of propanol-(2) are treated with 14 g. of sodium methylate; the methanol formed is removed by concentration in vacuo to half the volume and the suspension obtained is diluted with 250 ml. of methylene chloride. Then, 34.2 g. of 7-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid ethyl ester are added and the mixture is subsequently stirred at 25° C. for 40 minutes. The orange solution is made acidic with glacial acetic acid and evaporated to dryness under reduced pressure. The residue is partitioned between water and chloroform; the organic phase is washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and concentrated to dryness. The solid crude product is triturated with ether, removed by filtration, washed with ether and recrystallized from methylene chloride/ether, whereby there is obtained 7-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid isopropyl ester having a melting point of 234°-238° C. (decomposition).

Aufarbeitung

  1. customis removed by concentration in vacuo to half the volume
  2. customthe suspension obtained
  3. additionis diluted with 250 ml
  4. customevaporated to dryness under reduced pressure
  5. customThe residue is partitioned between water and chloroform
  6. washthe organic phase is washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to dryness
  9. customThe solid crude product is triturated with ether
  10. customremoved by filtration
  11. washwashed with ether
  12. customrecrystallized from methylene chloride/ether

Quellen und Nachweise

ORD-Eintrag
ord-af8d9f629f914c4181715a3c284ad0ae
Quelldatensatz
uspto-grants-1978_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04077978

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