Dimethyl Sulfoxide → HCID 22168736, compound
Reaction equation
[CH:1]([C:3]1[NH:4][CH:5]=[CH:6][CH:7]=1)=[O:2].[OH-].[K+].CS(C)=O.[Br:14][CH2:15][CH2:16]Br>O>[Br:14][CH2:15][CH2:16][N:4]1[CH:5]=[CH:6][CH:7]=[C:3]1[CH:1]=[O:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-formylpyrrole (1 g), potassium hydroxide (2.3 g) and dry DMSO (20 mL) was stirred under nitrogen atmosphere. 1,2-dibromoethane (7.9 g) was added dropwise at 20-25° C. and stirred till the reaction is complete. Water (50 mL) was added and the reaction mixture was extracted with diethyl ether (3×50 mL). The combined organic layer was washed with water (30 mL), followed by brine (30 mL) and was dried over Na2SO4. The solvent was evaporated and the compound obtained was purified by column chromatography (silica gel 100-200) using ethyl acetate:hexane (2:8) as an eluent to obtain the title compound.
Workup
- stirringstirred till the reaction
- extractionthe reaction mixture was extracted with diethyl ether (3×50 mL)
- washThe combined organic layer was washed with water (30 mL)
- dry with materialwas dried over Na2SO4
- customThe solvent was evaporated
- customthe compound obtained
- customwas purified by column chromatography (silica gel 100-200)
Sources & evidence
- ORD record
- ord-67b04e3462c04d7fa7f724ff62e6d4ba
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06987123B2
Reaction notes
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