Modular synthesis of formamidines and their formation of stable organogels

Chemical Communications

Volumn , Issue 21, 2004, Pages 2514-2516

  Díaz, David D ^a   Finn, M G ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FORMAMIDINE; ORGANIC COMPOUND; ORGANIC SOLVENT; SOLVENT;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; DRUG HYDROLYSIS; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; GEL; HYDROGEN BOND; PRECIPITATION; REACTION ANALYSIS; REPRODUCIBILITY; SOLVENT EFFECT; TECHNIQUE; TEMPERATURE DEPENDENCE;

EID: 9444272291     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b406704e     Document Type: Article

References (26)

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13. Compound 5 was synthesized by refluxing N,N-dimethylformamide dimethyl acetal with benzylamine for 13 h, see ref. 2.
14. See ESI† for details.
15. 2 (68.6 mg, 0.31 mmol) anda catalytic amount of DMAP (3.8 mg, 0.1 equiv.) added in one portion. The initial cloudy solution turned clear within 1 min and was stirred under reflux. Within 1 h, compound 11 started to precipitate from the hot solution. After 15 h, the solution was cooled to room temperature and the precipitate was filtered and washed with anhydrous acetonitrile and diethyl ether. The solid was dried at 50 °C, yielding 11 in 47% yield asa white hygroscopic material, which was stored under nitrogen at -20 °C. Omission of catalytic base (DMAP in this case) requires the use of significantly longer reaction times to achieve comparable yields. Selected characterization data of new compounds are provided in the ESI†.
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26. 2O for several days.