Synthesis of 5-benzylidene-3-(3-fluoro-4-yl-morpholin-4-yl-phenylimino)- thiazolidin-4-one derivatives catalyzed by [BmIm]OH and their anti-microbial activity

Chinese Chemical Letters

Volumn 22, Issue 8, 2011, Pages 883-886

  Patil, Sudhakar G ^a   Bagul, Rahul R ^a   Swami, Mangesh S ^a   Kotharkar, Nandini ^b   Darade, Kalpana ^b  

^a Organic Chemistry Research Laboratory   (India)

^b G H Raisoni Institute Interdisciplinary Sciences   (India)

Author keywords

bmIm OH; Anti bacterial; Anti fungal; Antimicrobials; Basic ionic liquid; Iminothizolidin 4 one

Indexed keywords

EID: 79958119298     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2011.03.002     Document Type: Article

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30. The solution 2-fluoro-4-morpholin-4-yl-phenylamine (3) (1 mmol) and ethyl bromoacetate (1.1 mmol) in [bmIm]OH (2 mmol) was stirred at rt. After 6 h cold water was added and extracted with ethyl acetate (3× 10 mL), washed with brine and dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography using petroleum ether: ethyl acetate (20:1) eluent to get pure iminothiazolidin-4-one (5). Aqueous layer was re-extracted with ether (3× 10 mL) to remove organic impurities and dried under vacuum at 90 °C to get pure ionic liquid.
31. A mixture iminothiazolidin-4-one (5) (1 mmol) and aldehyde (1.1 mmol) in [bmIm]OH (2 mmol) was stirred at rt. After 3 h cold water was added and residue was filtered dried and recrystalized from hot ethanol to get pure 5-benzylidene-3-(3-fluoro-4-yl-morpholin-4-yl-phenylimino)-thiazolidin-4-one (6). Aqueous layer was re-extracted with ether (3× 10 mL) to remove organic impurities and dried under vacuum at 90 °C to get pure ionic liquid.
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33. ++1]; IR (KBr): 3403, 3174, 2955, 2891, 2837, 2700, 2360, 2251, 1701, 1633, 1602, 1114, 923.