3-Chloropropionyl chloride → 5-(3-chloro-propionyl)-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

HRID 1071915Notizen

Reaktionsgleichung

[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.[Cl:17][CH2:18][CH2:19][C:20](Cl)=[O:21]>C1COCC1>[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([C:20](=[O:21])[CH2:19][CH2:18][Cl:17])[C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

The synthesis was performed according to the below synthetic scheme. To a solution of 11-Oxo-10,11-dihydro-5H-dibenzo[b,e][1,4] diazepin (0.376 gr., 1.79 mmol) in dry THF, (10 ml) NaNH2 (0.132 gr., 3.39 mmol) was added. The mixture was cooled to 0° C., and 0.2 ml 3-chloropropionyl chloride (2.09 mmol) was added dropwise. The mixture was stirred for 30 min at 0° C., allowed warming to room temperature, washed with 5% aq. potassium bicarbonate and extracted with CH2Cl2 (20 ml). The resulting organic layer was dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was crystallized from ether, resulting in 0.467 gr. (87% yield) of 11-Oxo-10,11-dihydro-5-[(3-chloro)1-oxopropyl] 5-H-dibenzo[b,e] [1,4] diazepin in the form of a yellow solid, mp 241-242° C. 1H NMR (CDCl3): 8.78 (s, 1H), 7.98 (s, 1H), 7.59 (s, 1H), 7.4-7.26 (m, 6H), 3.77 (m, 4H). FAB/MS: 301(M+).

Aufarbeitung

temperatureallowed warming to room temperature
washwashed with 5% aq. potassium bicarbonate
extractionextracted with CH2Cl2 (20 ml)
dry with materialThe resulting organic layer was dried over Na2SO4
filtrationfiltered
customthe solvent was removed under reduced pressure
customThe crude product was crystallized from ether
customresulting in 0.467 gr

Quellen und Nachweise

ORD-Eintrag: ord-7680762a90554e3fb1c78b50b2b7f26a
Quelldatensatz: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06908915B1

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