No renderable structure data available
C1=CC=C(C=C1)C2=CC=CC=C2S(=O)(=O)NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-phenylbenzenesulfonamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 40182-06-7 |
| Database ID | 12371520 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-phenylbenzenesulfonamide (CAS 40182-06-7) 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 12371520
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-89ca953036524beda998b25c8aaa2c0dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 23.3 g of 2-biphenylylsulfonamide, 10.9. g of n-butyl isocyanate, a catalytic amount of 1,4-diazabicyclo[2,2,2]-octane and 180 ml of chlorobenzene were refluxed with stirring for 2 hours. Then, phosgene in a slight excess of the theroretical amount was blown through the reaction mixture over 2 hours while maintaining the internal temperature at 115°-120° C. At this time, any unreacted phosgene escaping from the reaction system was trapped in a dry ice trap and returned to the reactor. After addition of the phosgene, the reaction mixture was further stirred at the reflux temperature for a short time to complete the reaction. The mixture was cooled, and if necessary, it was filtered under reduced pressure to remove the insoluble matter. It was then concentrated under reduced pressure, to obtain 20.0 g of 2-biphenylylsulfanylisocyanate, B.p 135°-137° C./0.7-0.8 mmHg. while maintaining the internal temperature at 115°-120° C the reaction mixture was further stirred at the reflux temperature for a short time the reaction The mixture was cooled if necessary, it was filtered under reduced pressure to remove the insoluble matter It was then concentrated under reduced pressure
Source ID: ord-b803ebad71d248dab033f98c2b32ba6cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 23.3 g of 2-biphenylylsulfonamide, 10.9. g of n-butyl isocyanate, a catalytic amount of 1,4-diazabicyclo[2,2,2]-octane and 180 ml of chlorobenzene were refluxed with stirring for 2 hours. Then, phosgene in a slight excess of the theroretical amount was blown through the reaction mixture over 2 hours while maintaining the internal temperature at 115°-120° C. At this time, any unreacted phosgene escaping from the reaction system was trapped in a dry ice trap and returned to the reactor. After addition of the phosgene, the reaction mixture was further stirred at the reflux temperature for a short time to complete the reaction. The mixture was cooled, and if necessary, it was filtered under reduced pressure to remove the insoluble matter. It was then concentrated under reduced pressure, to obtain 20.0 g of 2-biphenylylsulfanylisocyanate, B.p 135°-137° C./0.7-0.8 mmHg. while maintaining the internal temperature at 115°-120° C the reaction mixture was further stirred at the reflux temperature for a short time the reaction The mixture was cooled if necessary, it was filtered under reduced pressure to remove the insoluble matter It was then concentrated under reduced pressure
Source ID: ord-b803ebad71d248dab033f98c2b32ba6cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 23.3 g of 2-biphenylylsulfonamide, 10.9 g of n-butyl isocyanate, a catalytic amount of 1,4-diazabicyclo[2,2,2]-octane and 150 ml of xylene were refluxed with stirring for an hour. Then, a solution of 11.9 g of trichloromethyl chloroformate in 30 ml of xylene was added dropwise over 2.5 hours while maintaining the internal temperature at 120°-125° C. After this addition, the mixture was held at this temperature for a while, and thereafter the mixture was refluxed for a short period to complete the reaction. At the end of the reaction, the xylene and n-butyl isocyanate were distilled off under reduced pressure, to obtain 22.0 g of 2-biphenylylsulfonylisocyanate of high purity. B.pt. 135°-137° C./0.7-0.8 mmHg. while maintaining the internal temperature at 120°-125° C After this addition the mixture was refluxed for a short period the reaction At the end of the reaction the xylene and n-butyl isocyanate were distilled off under reduced pressure
Source ID: ord-22ef43056d5c40ca9171ede04b52abb2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 23.3 g of 2-biphenylylsulfonamide, 10.9 g of n-butyl isocyanate, a catalytic amount of 1,4-diazabicyclo[2,2,2]-octane and 150 ml of xylene were refluxed with stirring for an hour. Then, a solution of 11.9 g of trichloromethyl chloroformate in 30 ml of xylene was added dropwise over 2.5 hours while maintaining the internal temperature at 120°-125° C. After this addition, the mixture was held at this temperature for a while, and thereafter the mixture was refluxed for a short period to complete the reaction. At the end of the reaction, the xylene and n-butyl isocyanate were distilled off under reduced pressure, to obtain 22.0 g of 2-biphenylylsulfonylisocyanate of high purity. B.pt. 135°-137° C./0.7-0.8 mmHg. while maintaining the internal temperature at 120°-125° C After this addition the mixture was refluxed for a short period the reaction At the end of the reaction the xylene and n-butyl isocyanate were distilled off under reduced pressure
Source ID: ord-22ef43056d5c40ca9171ede04b52abb2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In Scheme 1 the compounds of the invention, 1, are prepared in 4 steps. Sulfonylation of valine methyl ester with 4-Bromo-benzenesulfonyl chloride was carried out under Hunig base condition to give sulfonamide intermediate 1. This 4-Bromo-benzenesulfonamide was furthered coupled with boronate ester using Palladium catalyst under Suzuki coupling condition to provide biphenyl sulfonamide Intermediate 2. Biphenyl sulfonamide intermediate 2 was then alkylated with various alkylating reagents to provide biphenyl sulfonamide ester (Intermediate 3). Hydrolysis of intermediate 3 was carried out using bases such as NaOH, or LiOH to afford the final product 1.
Source ID: ord-cb1561084d24494ab7f75e09f470b0aaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 23.3 g of 2-biphenylylsulfonamide, 10.9. g of n-butyl isocyanate, a catalytic amount of 1,4-diazabicyclo[2,2,2]-octane and 180 ml of chlorobenzene were refluxed with stirring for 2 hours. Then, phosgene in a slight excess of the theroretical amount was blown through the reaction mixture over 2 hours while maintaining the internal temperature at 115°-120° C. At this time, any unreacted phosgene escaping from the reaction system was trapped in a dry ice trap and returned to the reactor. After addition of the phosgene, the reaction mixture was further stirred at the reflux temperature for a short time to complete the reaction. The mixture was cooled, and if necessary, it was filtered under reduced pressure to remove the insoluble matter. It was then concentrated under reduced pressure, to obtain 20.0 g of 2-biphenylylsulfonylisocyanate. B.p. 135°-137° C./0.7-0.8 mmHg. while maintaining the internal temperature at 115°-120° C the reaction mixture was further stirred at the reflux temperature for a short time the reaction The mixture was cooled if necessary, it was filtered under reduced pressure to remove the insoluble matter It was then concentrated under reduced pressure
Source ID: ord-0f430a30c4d34f7aa045958fb0a72e5cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 23.3 g of 2-biphenylylsulfonamide, 10.9 g of n-butyl isocyanate, a catalytic amount of 1,4-diazabicyclo[2,2,2]-octane and 150 ml of xylene were refluxed with stirring for an hour. Then, a solution of 11.9 g of trichloromethyl chloroformate in 30 ml of xylene was added dropwise over 2.5 hours while maintaining the internal temperature at 120°-125° C. After this addition, the mixture was held at this temperature for a while, and thereafter the mixture was refluxed for a short period to complete the reaction. At the end of the reaction, the xylene and n-butyl isocyanate were distilled off under reduced pressure, to obtain 22.0 g of 2-biphenylylsulfonylisocyanate of high purity. B.pt. 135°-137° C./0.7-0.8 mmHg. while maintaining the internal temperature at 120°-125° C After this addition the mixture was refluxed for a short period the reaction At the end of the reaction the xylene and n-butyl isocyanate were distilled off under reduced pressure
Source ID: ord-d9785c6de781421fb99d9205510a39caConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sodium hydride (2.6 g) was added to dry dimethylformamide (200 ml), and at less than 10° C., a solution of 2-phenylbenzenesulfonamide (23.3 g) in dimethylformamide (50 ml) was added. The mixture was then stirred at room temperature for 1 hour, and diphenyl carbonate (21.4 g) was added at room temperature. The mixture was further stirred at room temperature for 1 hour. Then, after the whole mixture was added to ice water, the mixture was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was dehydrated, and ethyl acetate was distilled off under reduced pressure to give phenyl N-(2-biphenylylsulfonyl)carbamate (35 g) as a solidified desired compound represented by the following formula. mp. 114°-117° C. ##STR11## The mixture was further stirred at room temperature for 1 hour extracted with ethyl acetate ethyl acetate was distilled off under reduced pressure
Source ID: ord-b451aa9c8b1c4b67abab6a6e4f66cdaaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 23.3 g of 2-biphenylylsulfonamide, 10.9. g of n-butyl isocyanate, a catalytic amount of 1,4-diazabicyclo[2,2,2]-octane and 180 ml of chlorobenzene were refluxed with stirring for 2 hours. Then, phosgene in a slight excess of the theroretical amount was blown through the reaction mixture over 2 hours while maintaining the internal temperature at 115°-120° C. At this time, any unreacted phosgene escaping from the reaction system was trapped in a dry ice trap and returned to the reactor. After addition of the phosgene, the reaction mixture was further stirred at the reflux temperature for a short time to complete the reaction. The mixture was cooled, and if necessary, it was filtered under reduced pressure to remove the insoluble matter. It was then concentrated under reduced pressure, to obtain 20.0 g of 2-biphenylylsulfonylisocyanate. B.p. 135°-137° C./0.7-0.8 mmHg. while maintaining the internal temperature at 115°-120° C the reaction mixture was further stirred at the reflux temperature for a short time the reaction The mixture was cooled if necessary, it was filtered under reduced pressure to remove the insoluble matter It was then concentrated under reduced pressure
Source ID: ord-35c9e98dc0e14b8ea55cba1d7f3e5a81Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 23.3 g of 2-biphenylylsulfonamide, 10.9. g of n-butyl isocyanate, a catalytic amount of 1,4-diazabicyclo[2,2,2]-octane and 180 ml of chlorobenzene were refluxed with stirring for 2 hours. Then, phosgene in a slight excess of the theroretical amount was blown through the reaction mixture over 2 hours while maintaining the internal temperature at 115°-120° C. At this time, any unreacted phosgene escaping from the reaction system was trapped in a dry ice trap and returned to the reactor. After addition of the phosgene, the reaction mixture was further stirred at the reflux temperature for a short time to complete the reaction. The mixture was cooled, and if necessary, it was filtered under reduced pressure to remove the insoluble matter. It was then concentrated under reduced pressure, to obtain 20.0 g of 2-biphenylylsulfonylisocyanate. B.p. 135°-137° C./0.7-0.8 mmHg. while maintaining the internal temperature at 115°-120° C the reaction mixture was further stirred at the reflux temperature for a short time the reaction The mixture was cooled if necessary, it was filtered under reduced pressure to remove the insoluble matter It was then concentrated under reduced pressure
Source ID: ord-35c9e98dc0e14b8ea55cba1d7f3e5a81Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 23.3 g of 2-biphenylylsulfonamide, 10.9 g of n-butyl isocyanate, a catalytic amount of 1,4-diazabicyclo[2,2,2]-octane and 150 ml of xylene were refluxed with stirring for an hour. Then, a solution of 11.9 g of trichloromethyl chloroformate in 30 ml of xylene was added dropwise over 2.5 hours while maintaining the internal temperature at 120°-125° C. After this addition, the mixture was held at this temperature for a while, and thereafter the mixture was refluxed for a short period to complete the reaction. At the end of the reaction, the xylene and n-butyl isocyanate were distilled off under reduced pressure, to obtain 22.0 g of 2-biphenylylsulfonylisocyanate of high purity. B.pt. 135°-137° C./0.7-0.8 mmHg. while maintaining the internal temperature at 120°-125° C After this addition the mixture was refluxed for a short period the reaction At the end of the reaction the xylene and n-butyl isocyanate were distilled off under reduced pressure
Source ID: ord-038007230513477d8ac92249f5e9abc3PubChem References
These sources are listed in the compound's public database record.
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