Reaction #4168084
Related Literature (1)
openreactiondata ↗doi:10.1039/C8SC04228D
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-cf9eed5376c54db589f254b5cda630c6No renderable structure data available
C1=CC=C(C=C1)N2C(=O)C=CC2=OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 1-phenylpyrrole-2,5-dione |
|---|---|
| IUPAC Name | — |
| CAS Number | 941-69-5 |
| Database ID | 13662 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
1-phenylpyrrole-2,5-dione (CAS 941-69-5) 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 13662
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-cf9eed5376c54db589f254b5cda630c6Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6df9703ae37b43a0b556d48d8e7a88d6Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0841e96869224e0b9c41c228787fc6b4Conditions: temp:175.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 26.6 parts of the compound ##STR5## (from aniline and N-phenyl maleic imide) are dissolved in 100 ml of o-dichlorobenzene. 11.9 parts of phenylisocyanate are added and the reaction mixture is left to stand overnight. After the addition of 0.1 g of 1,4-diaza-bicyclo-[2,2,2]-octane, the solution is stirred for 6 hours at 175° C., the solvent is distilled off under vacuum and toluene is added to the residue. The crystalline precipitate obtained is suction filtered and recrystallised from ethyl acetate. The structure obtained by calculation is confirmed by the NMR- and IR-spectra (for hydantoin 1715 and 1770 cm-1 ; for amide 1690 cm-1). the reaction mixture is left the solvent is distilled off under vacuum and toluene is added to the residue The crystalline precipitate obtained filtered recrystallised from ethyl acetate The structure obtained by calculation
Source ID: ord-e5e0af98372b4a34ac73984ae3dbad52Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 7 ml of xylene was added to a mixture of 1.5 g of 2-[1-(2,4-dichlorophenyl)vinyl]indole and 1.0 g of N-phenylmaleimide. The resulting mixture was refluxed for 1 hour. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from isopropyl alcohol to obtain 1.2 g (yield: 50%) of N-phenyl-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydro-carbazole-3,4-dicarboximide as colorless crystal. The resulting mixture was refluxed for 1 hour The solvent was removed by distillation under reduced pressure The residue was recrystallized from isopropyl alcohol
Source ID: ord-0fd4b345d32a4e4f90cdd944df9f8b30Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-cf9eed5376c54db589f254b5cda630c6Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6df9703ae37b43a0b556d48d8e7a88d6Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 0.5-liter reactor equipped with a stirrer were placed 100 ml of styrene and 6.0 mmol as aluminum atom of methylaluminoxane obtained in the above Example 1 (1), and the resultant was stirred at the polymerization temperature of 30° C. for 30 minutes. Subsequently, 0.03 mmol as titanium atom of pentamethylcyclopentadienyltitanium trimethoxide was added. At the same time, 100 g of N-phenylmaleimide was dissolved in 300 ml of toluene, and after sufficiently replaced with nitrogen, this solution was added and polymerization was carried out at 40° C. for 5 hours with stirring. After the reaction was over, methanol was poured to stop the reaction. Further, a mixture of methanol-hydrochloric acid was added to decompose the catalyst components. Then, washing with methanol was repeated three times. The yield of thus obtained styrene-N-phenylmaleimide copolymer was 51.5 g. Intrinsic viscosity measured in 1,2,4-trichlorobenzene at 135° C. was 0.66 dl/g. In a 0.5-liter reactor equipped with a stirrer this solution was added polymerization was carried out at 40° C. for 5 hours with stirring was poured the reaction was added Then, washing with methanol measured in 1,2,4-trichlorobenzene at 135° C.
Source ID: ord-9c5306a4ab61488489a7c59b5827c848Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 0.5-liter reactor equipped with a stirrer were placed 100 ml of styrene and 6.0 mmol as aluminum atom of methylaluminoxane obtained in the above Example 1 (1), and the resultant was stirred at the polymerization temperature of 30° C. for 30 minutes. Subsequently, 0.03 mmol as titanium atom of pentamethylcyclopentadienyltitanium trimethoxide was added. At the same time, 100 g of N-phenylmaleimide was dissolved in 300 ml of toluene, and after sufficiently replaced with nitrogen, this solution was added and polymerization was carried out at 40° C. for 5 hours with stirring. After the reaction was over, methanol was poured to stop the reaction. Further, a mixture of methanol-hydrochloric acid was added to decompose the catalyst components. Then, washing with methanol was repeated three times. The yield of thus obtained styrene-N-phenylmaleimide copolymer was 51.5 g. Intrinsic viscosity measured in 1,2,4-trichlorobenzene at 135° C. was 0.66 dl/g. In a 0.5-liter reactor equipped with a stirrer this solution was added polymerization was carried out at 40° C. for 5 hours with stirring was poured the reaction was added Then, washing with methanol measured in 1,2,4-trichlorobenzene at 135° C.
Source ID: ord-9c5306a4ab61488489a7c59b5827c848Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 17.3 parts of N-phenyl maleic imide and 8.8 parts of N,N'-dimethyl urea in 100 parts of cresol is stirred for three hours at 190° C. The solvent is distilled off in vacuo and the residue fractionated. The oily liquid which distills at a boiling point of 220° C./0.1 Torr solidifies after a while and may be recrystallised from n-propanol (Mp. 114°-115° C.). IR and NMR-spectra confirm the assumed compound. The solvent is distilled off in vacuo The oily liquid which distills at a boiling point of 220° C./0.1 Torr may be recrystallised from n-propanol (Mp. 114°-115° C.)
Source ID: ord-8b024fb737aa439eb142cfe6c438d4a7Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 17.3 parts of N-phenyl maleic imide and 8.8 parts of N,N'-dimethyl urea in 100 parts of cresol is stirred for three hours at 190° C. The solvent is distilled off in vacuo and the residue fractionated. The oily liquid which distills at a boiling point of 220° C./0.1 Torr solidifies after a while and may be recrystallised from n-propanol (Mp. 114°-115° C.). IR and NMR-spectra confirm the assumed compound. The solvent is distilled off in vacuo The oily liquid which distills at a boiling point of 220° C./0.1 Torr may be recrystallised from n-propanol (Mp. 114°-115° C.)
Source ID: ord-8b024fb737aa439eb142cfe6c438d4a7Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A reaction flask was equipped as in Example 1. To a solution of maleic anhydride (1.12 parts) in 5.6 parts acetone was added a solution of 1 part aniline, 0.375 part triethylamine, and 1.9 parts acetone over a 30-minute period. The resulting heterogeneous mixture was maintained at 40° C. for 30 minutes. Magnesium chloride hexahydrate (0.093 part) and 1.4 parts acetic anhydride were added all at once. The temperature was raised to 50° C. for 3 hours. The homogeneous mixture was cooled and 14 parts water added. The precipitated product was isolated by vacuum filtration, washed with water, and air dried. The crude product was recrystallized from ethanol/water (90/10 vol.) to yield 0.89 part N-phenyl maleimide, m.p. 84°-86° C. A reaction flask was equipped as in Example 1 The temperature was raised to 50° C. for 3 hours The homogeneous mixture was cooled The precipitated product was isolated by vacuum filtration washed with water, and air dried The crude product was recrystallized from ethanol/water (90/10 vol.)
Source ID: ord-70da2d85e5dc485d8ae20fa76713538fPubChem References
These sources are listed in the compound's public database record.
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