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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 25070Generated: October 26, 2026

Dimethylformamide → (+/-)-7-(5,6-Dihydro-4-oxo-4H-1,3-thiazin-2-yl)-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

https://huagongshe.com/reaction/25070

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantEthyl 3-bromopropionateHCID 68320—
Reactant(+/-)-8-Methyl-5-(4-nitrophenyl)-7-thiocarbamoyl-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepineHCID 12137394—
SolventSodium ChlorideHCID 5234—
Product(+/-)-7-(5,6-Dihydro-4-oxo-4H-1,3-thiazin-2-yl)-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepineHCID 2256550259%

Reaction Conditions

Temperature85 °C

Reaction Steps

A mixture of 2.00 g (5.20 mmol) of the starting material I, 1.89 g (10.44 mmol) of ethyl 3-bromopropionate and 20 ml of dimethylformamide was stirred at 80-90° C. for 3 h. The reaction mixture was diluted with 25% sodium chloride solution and extracted with dichloromethane. After drying and concentration the crude product was purified by column chromatography using silica gel (MN Kieselgel 60) as adsorbent and a mixture of ethyl acetate-methanol (2:1) as eluent to yield 1.34 g (59%) of the title compound; Mp.: 220-221° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06858605B2
Source datasetuspto-grants-2005_02
ORD IDord-6e91e6ae17d04701a181c4bd260236a7
Source noteuspto-grants-2005_02