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Phosgene → 8-Chloro-6-(2-chlorophenyl)-1,2-dihydro-1-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid methyl ester

HRID 26047
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 26047
N[CH2:2][O:3][C:4]([CH:6]=[C:7]1[CH2:13][N:12]=[C:11]([C:14]2C=[CH:18][CH:17]=[CH:16][C:15]=2Cl)[C:10]2[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:9]=2[NH:8]1)=[O:5].O1C(C[O:30][C:31]2C=CC=CC=2)C1.[C:37]([Cl:40])(Cl)=O.[OH-].[NH4+:42].[K+].[Br-]>C(Cl)Cl.C1C=CC=CC=1>[CH3:2][O:3][C:4]([C:6]1[NH:42][C:31](=[O:30])[N:8]2[C:9]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:10]=3[C:11]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:37]=3[Cl:40])=[N:12][CH2:13][C:7]=12)=[O:5]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 6371PhosgeneHCID 14923Ammonium HydroxideHCID 31217Phenyl glycidyl etherHCID 253877Potassium BromideHCID 700515042-[(amino)methoxycarbonylmethylene]-7-chloro-5-(2-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine

Produkt 1

HCID 12703475
8-Chloro-6-(2-chlorophenyl)-1,2-dihydro-1-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirred solution of 15 g (0.04 mole) of 2-[(amino)methoxycarbonylmethylene]-7-chloro-5-(2-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine and 12 g (0.08 mole) of 1,2-epoxy-3-phenoxypropane in 150 ml of methylene chloride was cooled in an ice-salt bath and treated with 47 g (0.06 mole) of a 12.5% solution of phosgene in benzene at a moderate rate. Stirring in the cold under a drying tube was continued for 2 hours. A cold solution of 3N ammonium hydroxide (50 ml) was added and stirring was continued for 10 min. The organic phase was separated, dried over sodium sulfate and evaporated under reduced pressure. Stirring the oily residue with anhydrous ether gave off-white crystals. The crystals were filtered, washed with ether and air dried on the funnel to yield the end product. Recrystallization from ethanol methylene chloride gave white needles with mp 273°-276° (dec). Uv λ max 223 mμ (ε=43800) 276 (21100) infl 348 (1100) ir (KBr) 3150 (NH) 1720 (COOMe, CO) nmr (CDCl3) δ 3.80 ppm (s, 3, OCH3) 4.11 (broad d, 1) and 5.58 (broad d, 1) (AB-system, J=12 Hz, C4 -H) 6.95 (d, 1, J=2.5 Hz, C7 -H) 7.3-7.8 (m, 5, aromatic H) 7.96 (d, 1, J=8 Hz, C10 -H) 11.19 (broad s, 1, NH).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 10 min
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. stirringStirring the oily residue with anhydrous ether
  7. customgave off-white crystals
  8. filtrationThe crystals were filtered
  9. washwashed with ether and air
  10. customdried on the funnel
  11. customto yield the end product
  12. customRecrystallization from ethanol methylene chloride
  13. customgave white needles with mp 273°-276° (dec)

Quellen und Nachweise

ORD-Eintrag
ord-67330f99046c476a8877197d20621a66
Quelldatensatz
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04147875

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