| Identification | Back Directory | [Name]
(2-Butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone | [CAS]
141627-42-1 | [Synonyms]
Dronedaron Impurity E
Dronedarone Impurity E
Dronedarone Impurity 22
2-butyl-3-(4-methoxybenzoyl)-5-nitrobenzofuran
2-butyl-3-[(4-Methoxyphenyl)carbonyl]-5-nitro-1-benzofuran
(2-butyl-5-nitro-3-benzofuranyl)(4-methoxyphenyl)Methanone
(2-Butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone
Methanone, (2-butyl-5-nitro-3-benzofuranyl)(4-methoxyphenyl)-
(2-butyl-5-nitro-1-benzofuran-3-yl)-(4-methoxyphenyl)methanone
(2-Butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone (BNB-V)
Methanone,(2-butyl-5-nitro-3-benzofuranyl)(4-methoxyphenyl)- CAS 141627-42-1 | [EINECS(EC#)]
604-241-8 | [Molecular Formula]
C20H19NO5 | [MDL Number]
MFCD14525623 | [MOL File]
141627-42-1.mol | [Molecular Weight]
353.37 |
| Chemical Properties | Back Directory | [Boiling point ]
537.7±50.0 °C(Predicted) | [density ]
1.234±0.06 g/cm3(Predicted) | [storage temp. ]
Storage temp. 2-8°C | [Appearance]
Yellow to brown Solid | [InChI]
InChI=1S/C20H19NO5/c1-3-4-5-18-19(20(22)13-6-9-15(25-2)10-7-13)16-12-14(21(23)24)8-11-17(16)26-18/h6-12H,3-5H2,1-2H3 | [InChIKey]
WYALRXZJYXWYGR-UHFFFAOYSA-N | [SMILES]
C(C1C2=CC([N+]([O-])=O)=CC=C2OC=1CCCC)(C1=CC=C(OC)C=C1)=O |
| Hazard Information | Back Directory | [Uses]
(2-Butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone is a reagent in the preparation of heterocyclic benzofuran carboxamides via amidation of heterocyclic acyl chlorides with benzofuranamine. This is also a derivative of Dronedarone (D679445),which is a drug used for the treatment of atrial fibrillation and atrial flutter in patients who have suffered cardiac arrhythmias. | [Synthesis]
Method-2: A solution of 45 g (0.2 mol) of 2-butyl-5-nitrobenzofuran and 44 g of p-methoxybenzoyl chloride in 300 ml of chlorobenzene was added to a round bottomed flask at 25 °C. To the reaction mixture was slowly added a solution of 40 g of aluminum chloride in 300 ml of chlorobenzene. The reaction system was heated to reflux for 2 hours, subsequently cooled to room temperature and diluted with 40 ml of water. The organic phase was separated and washed sequentially with water and 5% sodium bicarbonate solution. The organic phase was concentrated to dryness under reduced pressure and the resulting product was rapidly crystallized. By recrystallization from 270 ml of isopropanol, 2-butyl-3-(4-methoxybenzoyl)-5-nitrobenzofuran was obtained with a melting point of 94-96°C and HPLC purity >96%. | [References]
[1] Patent: WO2012/32545, 2012, A1. Location in patent: Page/Page column 32
[2] Journal of the Chinese Chemical Society, 2011, vol. 58, # 7, p. 841 - 845
[3] Patent: US5223510, 1993, A
[4] Journal of Chemical Sciences, 2012, vol. 124, # 5, p. 1077 - 1085
[5] Organic Process Research and Development, 2014, vol. 18, # 1, p. 157 - 162 |
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