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CC1=CNC=C1CChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3,4-dimethyl-1H-pyrrole |
|---|---|
| IUPAC Name | — |
| CAS Number | 822-51-5 |
| Database ID | 5324584 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3,4-dimethyl-1H-pyrrole (CAS 822-51-5) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 5324584
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-19a77e6608064806bce791207986bb70Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 0.92 mL (12 mmoles) of N,N-dimethylformamide in 10 mL of 1,2-dichloroethane was added dropwise 1.0 mL (12 mmoles) of phosphorus oxychloride at 0° C. The ice-bath was removed and the reaction mixture was further stirred for 30 min. 3,4-Dimethylpyrrole (960.0 mg, 10 mmoles) was added to the above solution portionwise and the reaction mixture was stirred at 50° C. for 5 h. The reaction mixture was poured into ice-cold 1N sodium hydroxide solution (pH=9 after mixing) and the resulting mixture was stirred at room temperature for 1 h. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine until pH=7, dried over anhydrous sodium sulfate and evaporated. The residue was chromatographed on a silica gel column eluting with a solvent mixture of ethyl acetate and hexane to afford 610 mg (50%) of the title compound. The ice-bath was removed the reaction mixture was stirred at 50° C. for 5 h the resulting mixture was stirred at room temperature for 1 h The organic layer was separated the aqueous layer was extracted with ethyl acetate The combined organic layer was washed with brine until pH=7 dried over anhydrous sodium sulfate evaporated The residue was chromatographed on a silica gel column eluting with a solvent mixture of ethyl acetate and hexane
Source ID: ord-a1b360f0bff8425180fb21395b856871Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Based on D. O. Cheng, T. L. Bowman, E. LeGoff, J. Heterocyclic Chem. 13, 1145 (1976), 3,4-dimethylpyrrole was synthesized starting from p-toluol-sulfonylmethyliso-cyanide and crotonic-acid-ethyl-ester. The dimethyl compound was quickly obtained after reduction of the intermediary 3-(ethoxycarbonyl)-4-methylpyrrole, but at only 18% total yield. The material had a melting point of 25°-28° C. H-NMR (CDCl3): 2.04 (s, 6H), 6.50 (d, 2H), 7.33 (s br, 1H).
Source ID: ord-5f12b5c4b65f4ad3aa4980da30b05451Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 0.92 mL (12 mmoles) of N,N-dimethylformamide in 10 mL of 1,2-dichloroethane was added dropwise 1.0 mL (12 mmoles) of phosphorus oxychloride at 0° C. The ice-bath was removed and the reaction mixture was further stirred for 30 min. 3,4-Dimethylpyrrole (960.0 mg, 10 mmoles) was added to the above solution portionwise and the reaction mixture was stirred at 50° C. for 5 h. The reaction mixture was poured into ice-cold 1N sodium hydroxide solution (pH=9 after mixing) and the resulting mixture was stirred at room temperature for 1 h. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine until pH=7, dried over anhydrous sodium sulfate and evaporated. The residue was chromatographed on a silica gel column eluting with a solvent mixture of ethyl acetate and hexane to afford 610 mg (50%) of the title compound. The ice-bath was removed the reaction mixture was stirred at 50° C. for 5 h the resulting mixture was stirred at room temperature for 1 h The organic layer was separated the aqueous layer was extracted with ethyl acetate The combined organic layer was washed with brine until pH=7 dried over anhydrous sodium sulfate evaporated The residue was chromatographed on a silica gel column eluting with a solvent mixture of ethyl acetate and hexane
Source ID: ord-11660045273e4360bd4c42b9e7bdf02eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 0.92 mL (12 mmoles) of N,N-dimethylformamide in 10 mL of 1,2-dichloroethane was added dropwise 1.0 mL (12 mmoles) of phosphorus oxychloride at 0° C. The ice-bath was removed and the reaction mixture was further stirred for 30 min. 3,4-Dimethylpyrrole (960.0 mg, 10 mmoles) was added to the above solution portionwise and the reaction mixture was stirred at 50° C. for 5 h. The reaction mixture was poured into ice-cold 1N sodium hydroxide solution (pH=9 after mixing) and the resulting mixture was stirred at room temperature for 1 h. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine until pH=7, dried over anhydrous sodium sulfate and evaporated. The residue was chromatographed on a silica gel column eluting with a solvent mixture of ethyl acetate and hexane to afford 610 mg (50%) of the title compound. The ice-bath was removed the reaction mixture was stirred at 50° C. for 5 h the resulting mixture was stirred at room temperature for 1 h The organic layer was separated the aqueous layer was extracted with ethyl acetate The combined organic layer was washed with brine until pH=7 dried over anhydrous sodium sulfate evaporated The residue was chromatographed on a silica gel column eluting with a solvent mixture of ethyl acetate and hexane
Source ID: ord-11660045273e4360bd4c42b9e7bdf02eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 0.92 mL (12 mmoles) of N,N-dimethylformamide in 10 mL of 1,2-dichloroethane was added dropwise 1.0 mL (12 mmoles) of phosphorus oxychloride at 0° C. The ice-bath was removed and the reaction mixture was further stirred for 30 min. 3,4-Dimethylpyrrole (960.0 mg, 10 mmoles) was added to the above solution portionwise and the reaction mixture was stirred at 50° C. for 5 h. The reaction mixture was poured into ice-cold 1N sodium hydroxide solution (pH=9 after mixing) and the resulting mixture was stirred at room temperature for 1 h. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine until pH=7, dried over anhydrous sodium sulfate and evaporated. The residue was chromatographed on a silica gel column eluting with a solvent mixture of ethyl acetate and hexane to afford 610 mg (50%) of the title compound. The ice-bath was removed the reaction mixture was stirred at 50° C. for 5 h the resulting mixture was stirred at room temperature for 1 h The organic layer was separated the aqueous layer was extracted with ethyl acetate The combined organic layer was washed with brine until pH=7 dried over anhydrous sodium sulfate evaporated The residue was chromatographed on a silica gel column eluting with a solvent mixture of ethyl acetate and hexane
Source ID: ord-f67ae682dbce45afb353d2a45f43a96eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 0.92 mL (12 mmoles) of N,N-dimethylformamide in mL of 1,2-dichloroethane was added dropwise 1.0 mL (12 mmoles) of phosphorus oxychloride at 0°C. The ice-bath was removed and the reaction mixture was further stirred for 30 min. 3,4-Dimethylpyrrole (960.0 mg, 10 mmoles) was added to the above solution portionwise and the reaction mixture was stirred at 50° C. for 5 h. The reaction mixture was poured into ice-cold 1N sodium hydroxide solution (pH=9 after mixing) and the resulting mixture was stirred at room temperature for 1 h. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine until pH=7, dried over anhydrous sodium sulfate and evaporated. The residue was chromatographed on a silica gel column eluting with a solvent mixture of ethyl acetate and hexane to afford 610 mg (50%) of the title compound. The ice-bath was removed the reaction mixture was stirred at 50° C. for 5 h the resulting mixture was stirred at room temperature for 1 h The organic layer was separated the aqueous layer was extracted with ethyl acetate The combined organic layer was washed with brine until pH=7 dried over anhydrous sodium sulfate evaporated The residue was chromatographed on a silica gel column eluting with a solvent mixture of ethyl acetate and hexane
Source ID: ord-f8448572e84d42ae8d3459ece5e34daaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 0.92 mL (12 mmoles) of N,N-dimethylformamide in 10 mL of 1,2-dichloroethane was added dropwise 1.0 mL (12 mmoles) of phosphorus oxychloride at 0° C. The ice-bath was removed and the reaction mixture was further stirred for 30 min. 3,4-Dimethylpyrrole (960.0 mg, 10 mmoles) was added to the above solution portionwise and the reaction mixture was stirred at 50° C. for 5 h. The reaction mixture was poured into ice-cold 1N sodium hydroxide solution (pH=9 after mixing) and the resulting mixture was stirred at room temperature for 1 h. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine until pH=7, dried over anhydrous sodium sulfate and evaporated. The residue was chromatographed on a silica gel column eluting with a solvent mixture of ethyl acetate and hexane to afford 610 mg (50%) of the title compound. The ice-bath was removed the reaction mixture was stirred at 50° C. for 5 h the resulting mixture was stirred at room temperature for 1 h The organic layer was separated the aqueous layer was extracted with ethyl acetate The combined organic layer was washed with brine until pH=7 dried over anhydrous sodium sulfate evaporated The residue was chromatographed on a silica gel column eluting with a solvent mixture of ethyl acetate and hexane
Source ID: ord-a1b360f0bff8425180fb21395b856871Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Based on D. O. Cheng, T. L. Bowman, E. LeGoff, J. Heterocyclic Chem. 13, 1145 (1976), 3,4-dimethylpyrrole was synthesized starting from p-toluol-sulfonylmethyliso-cyanide and crotonic-acid-ethyl-ester. The dimethyl compound was quickly obtained after reduction of the intermediary 3-(ethoxycarbonyl)-4-methylpyrrole, but at only 18% total yield. The material had a melting point of 25°-28° C. H-NMR (CDCl3): 2.04 (s, 6H), 6.50 (d, 2H), 7.33 (s br, 1H).
Source ID: ord-5f12b5c4b65f4ad3aa4980da30b05451Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-19a77e6608064806bce791207986bb70Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 0.92 mL (12 mmoles) of N,N-dimethylformamide in 10 mL of 1,2-dichloroethane was added dropwise 1.0 mL (12 mmoles) of phosphorus oxychloride at 0° C. The ice-bath was removed and the reaction mixture was further stirred for 30 min. 3,4-Dimethylpyrrole (960.0 mg, 10 mmoles) was added to the above solution portionwise and the reaction mixture was stirred at 50° C. for 5 h. The reaction mixture was poured into ice-cold 1N sodium hydroxide solution (pH=9 after mixing) and the resulting mixture was stirred at room temperature for 1 h. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine until pH=7, dried over anhydrous sodium sulfate and evaporated. The residue was chromatographed on a silica gel column eluting with a solvent mixture of ethyl acetate and hexane to afford 610 mg (50%) of the title compound. The ice-bath was removed the reaction mixture was stirred at 50° C. for 5 h the resulting mixture was stirred at room temperature for 1 h The organic layer was separated the aqueous layer was extracted with ethyl acetate The combined organic layer was washed with brine until pH=7 dried over anhydrous sodium sulfate evaporated The residue was chromatographed on a silica gel column eluting with a solvent mixture of ethyl acetate and hexane
Source ID: ord-7cb84ba9c7c6438c8a74a68beb413704Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 0.92 mL (12 mmoles) of N,N-dimethylformamide in 10 mL of 1,2-dichloroethane was added dropwise 1.0 mL (12 mmoles) of phosphorus oxychloride at 0° C. The ice-bath was removed and the reaction mixture was further stirred for 30 min. 3,4-Dimethylpyrrole (960.0 mg, 10 mmoles) was added to the above solution portionwise and the reaction mixture was stirred at 50° C. for 5 h. The reaction mixture was poured into ice-cold 1 N sodium hydroxide solution (pH=9 after mixing) and the resulting mixture was stirred at room temperature for 1 h. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine until pH=7, dried over anhydrous sodium sulfate and evaporated. The residue was chromatographed on a silica gel column eluting with a solvent mixture of ethyl acetate and hexane to afford 610 mg (50%) of the title compound. The ice-bath was removed the reaction mixture was stirred at 50° C. for 5 h the resulting mixture was stirred at room temperature for 1 h The organic layer was separated the aqueous layer was extracted with ethyl acetate The combined organic layer was washed with brine until pH=7 dried over anhydrous sodium sulfate evaporated The residue was chromatographed on a silica gel column eluting with a solvent mixture of ethyl acetate and hexane
Source ID: ord-3dee32b1acdc4e498854609e2e1e90e7PubChem References
These sources are listed in the compound's public database record.
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