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Showing posts with label 4-dione. Show all posts
Showing posts with label 4-dione. Show all posts

Friday 1 January 2016

3-Fluoro-1-H-1,5-benzodiazepine-2,4-dione



3-Fluoro-1-H-1,5-benzodiazepine-2,4-dione

 

 

 

o-Phenylenediamine (2.70 g, 25 mmol) was added to the solution of sodium (1.2 g, 53 mmol) in anhydrous ethanol (50 mL) and the mixture was heated to reflux. Diethyl 2-fluoromalonate (4.45 g, 25 mmol) was added dropwise over 10 minutes and the mixture was heated at reflux for 2 h. After cooling to room temperature, the solution was filtered, the residue was washed with ethanol (20 mL), dissolved in water (30 mL) and acidified with HCl to pH 1. The mixture was cooled in ice, filtered, washed with water (2 × 10mL) and dried in vacuo to afford 3-fluoro-1-H-1,5-benzodiazepine-2,4-dione (3.23 g, 68%) as a tan powder.

m.p.: >300 °C, ([M + H]+, 195.0567, C9H8FN2O2 requires: [M]+, 195.0570); 

IR (neat,cm−1) 3084, 2951, 1727, 1681, 1500, 1159;  


δH (DMSO d6, 400 MHz): 5.57 (1H, d, 2JHF 46.4, CHF), 7.15–7.19 (2H, m, Ar–H), 7.22 (2H, dt, 3JHH 6.6, 4JHH 3.5, Ar–H), 10.81 (2H, bs N–H); δF (DMSO d6, 376 MHz): – 207.99 (d, 2JHF 46.4 C–F);

 δC (DMSO d6, 100 MHz) 85.12 (d, 1JCF 184.5, C–F), 122.55, 125.52, 128.41, 163.36 (d, 2JCF 23.2, C[double bond, length as m-dash]O), 164.59 (d, 2JCF 13.4, C[double bond, length as m-dash]O); 

m/z (ASAP) 195 (100%, [M + H]+), 135 (23%, [M − COCHF]+)............   N. Ishikawa, A. Takaoka and M. K. Ibrahim, J. Fluorine Chem., 1984, 25, 203–212 CrossRef CAS.


 http://pubs.rsc.org/en/content/articlehtml/2015/gc/c5gc00402k





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Tuesday 12 August 2014

7-Phenyl-1 3-diazaspiro[4.4]nonane-2,4-dione

7-Phenyl-1 3-diazaspiro[4.4]nonane-2,4-dione




Figure US20020052370A1-20020502-C00183

The product from Preparation 83 (5.8 g), potassium cyanide (2.75 g) and ammonium carbonate (9.1 g) were heated in 80 mls of 50% aqueous EtOH for 7 h, and then at room temperature for 48 h. The mixture was filtered, and the solid washed thoroughly with water (3×50 mls). The filtrate was concentrated, the pH adjusted to 2 using concentrated HCl and the resulting suspension filtered off and washed with water (3×50 mls). The bulked solids were recrystallised from EtOH and water (300 ml:100 ml) to give the title product as 1:1 mixture of diatereoisomeric pairs (6.32 g); R0.6 in EtOAc;


 1HNMR (300 MHz, CDCl3) δ: 1.60-2.58 (m, 6H), 3.08-3.37 (m, 1H), 6.83-7.44 (m, 5H), 8.33 (d, 1H), 10.60 (s, 1H);