A novel and efficient strategy for the synthesis of various carbamates using carbamoyl chlorides under solvent-free and grinding conditions using microwave irradiation

New aminoporphyrins bearing urea derivative substituents: synthesis, characterization, antibacterial and antifungal activity

“…The reaction mixture was cooled at room temperature and filtered. The filtrate was evaporated in vacuo to dryness and the residue was washed with hot hexane to remove unreacted triphosgene; the mixture was filtered and the resulting residue was crystallized from hexane to give corresponding carbamoyl chloride (Scheme 2; a and b) (Zare et al 2012 …”

“…The reaction was stirred and refluxed in the presence of dry solid sodium hydroxide as mild catalyst (750 mg, 19 mmol) for 30 min to give corresponding carbamoyl chloride (Scheme 2, c and d) (Zare et al 2012). Dimethylcarbamoyl chloride (yellow liquid with a pungent odor, yield: 56%), bp: 167 ο C, IR (KBr, ν, cm -1 ): 680 (C-Cl), 1400 (C-N), 1500 (C=O), 3000 (C-H sp 3 ).…”

“…Compared to phosgene and diphosgene, it exhibits superior properties. Generally, aliphatic and aromatic carbamoyl chlorides are prepared from amines and phosgene group compounds by a simple one-step condensation method (Scheme 1) (Tilley and Sayigh 1963;Johnson 1967 (Zare et al 2012). The reactions were clean and only the carbamoyl chlorides were detected by spectroscopic analysis of the crude products.…”

Synthesis of N-Phenylcarbamate by C–N Coupling Reaction without Metal Participation

“…Methyl Diphenylcarbamate (3p). 31 Compound 3p was obtained from the reaction of diphenylamine (50.7 mg, 0.3 mmol) and carbazate 2a (1.5 mmol, 3.0 equiv. ), and purified by column chromatography (10:1 PE/EtOAc), obtained as a a yellow solid (40.9 mg, 60%), m.p.…”

“…13 C NMR (100 MHz, CDCl 3 ):  = 153. 81, 140.45, 138.81, 134.42, 124.23, 117.40, 115.92, 52.45, 21. Methyl Diphenylcarbamate (3p) 31 Compound 3p was obtained from the reaction of diphenylamine (50.7 mg, 0.3 mmol) and carbazate 2a (1.5 mmol, 3.0 equiv), and purified by column chromatography (10:1 PE/EtOAc). Yield: 40.9 mg (60%) yellow solid; mp 84.5-85 °C.…”