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Structure of 3-omega-Bromoacetylcoumarin
CAS No.: 29310-88-1
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 29310-88-1 |
Formula : | C11H7BrO3 |
M.W : | 267.08 |
SMILES Code : | O=C1C(C(CBr)=O)=CC2=C(O1)C=CC=C2 |
MDL No. : | MFCD00488331 |
InChI Key : | NTYOLVNSXVYRTJ-UHFFFAOYSA-N |
Pubchem ID : | 2063461 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H301-H311-H331-H341 |
Precautionary Statements: | P201-P202-P261-P264-P270-P271-P280-P302+P352-P304+P340-P308+P313-P310-P330-P361-P403+P233-P405-P501 |
Class: | 6.1 |
UN#: | 2811 |
Packing Group: | Ⅲ |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | General procedure: A mixture of thiochroman-4-one 1 (1 mmol), benzaldehyde 2(1 mmol), thiourea 3 (1 mmol) was stirred in presence of ionic liquid,[Bmim]HSO4 (1 mL) at 80 C for 20 min followed by the additionof 3-bromo-1-phenylpropan-1-one 4 (1 mmol) and theresulting mixture was further stirred at 80 C for 40-70 min. Theprogress of reaction was monitored by TLC. After completion ofthe reaction, the mixture was diluted with 20 mL of water,2 20 mL of EtOAc was added and shaken vigorously. The organiclayer was separated from the solution. The aqueous layer wasevaporated, the ionic liquid was dried at 60-70 C under vacuumand then reused. The results have shown that the [Bmim]HSO4ionic liquid could be reused at least for four times. The productwas purified by column chromatography on neutral alumina(100-200 mesh), eluted with a solvent system of ethyl acetate-hexane to afford the title compounds 5a-n. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | General procedure: A mixture of thiochroman-4-one 1 (1 mmol), benzaldehyde 2(1 mmol), thiourea 3 (1 mmol) was stirred in presence of ionic liquid,[Bmim]HSO4 (1 mL) at 80 C for 20 min followed by the additionof 3-bromo-1-phenylpropan-1-one 4 (1 mmol) and theresulting mixture was further stirred at 80 C for 40-70 min. Theprogress of reaction was monitored by TLC. After completion ofthe reaction, the mixture was diluted with 20 mL of water,2 20 mL of EtOAc was added and shaken vigorously. The organiclayer was separated from the solution. The aqueous layer wasevaporated, the ionic liquid was dried at 60-70 C under vacuumand then reused. The results have shown that the [Bmim]HSO4ionic liquid could be reused at least for four times. The productwas purified by column chromatography on neutral alumina(100-200 mesh), eluted with a solvent system of ethyl acetate-hexane to afford the title compounds 5a-n. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | General procedure: A mixture of thiochroman-4-one 1 (1 mmol), benzaldehyde 2(1 mmol), thiourea 3 (1 mmol) was stirred in presence of ionic liquid,[Bmim]HSO4 (1 mL) at 80 C for 20 min followed by the additionof 3-bromo-1-phenylpropan-1-one 4 (1 mmol) and theresulting mixture was further stirred at 80 C for 40-70 min. Theprogress of reaction was monitored by TLC. After completion ofthe reaction, the mixture was diluted with 20 mL of water,2 20 mL of EtOAc was added and shaken vigorously. The organiclayer was separated from the solution. The aqueous layer wasevaporated, the ionic liquid was dried at 60-70 C under vacuumand then reused. The results have shown that the [Bmim]HSO4ionic liquid could be reused at least for four times. The productwas purified by column chromatography on neutral alumina(100-200 mesh), eluted with a solvent system of ethyl acetate-hexane to afford the title compounds 5a-n. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | General procedure: A mixture of thiochroman-4-one 1 (1 mmol), benzaldehyde 2(1 mmol), thiourea 3 (1 mmol) was stirred in presence of ionic liquid,[Bmim]HSO4 (1 mL) at 80 C for 20 min followed by the additionof 3-bromo-1-phenylpropan-1-one 4 (1 mmol) and theresulting mixture was further stirred at 80 C for 40-70 min. Theprogress of reaction was monitored by TLC. After completion ofthe reaction, the mixture was diluted with 20 mL of water,2 20 mL of EtOAc was added and shaken vigorously. The organiclayer was separated from the solution. The aqueous layer wasevaporated, the ionic liquid was dried at 60-70 C under vacuumand then reused. The results have shown that the [Bmim]HSO4ionic liquid could be reused at least for four times. The productwas purified by column chromatography on neutral alumina(100-200 mesh), eluted with a solvent system of ethyl acetate-hexane to afford the title compounds 5a-n. |
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