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CN(C)S(=O)(=O)C1=CC=CC=C1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | N,N-dimethylbenzenesulfonamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 14417-01-7 |
| Database ID | 84423 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
N,N-dimethylbenzenesulfonamide (CAS 14417-01-7) 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 84423
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-700de64c73c8493eb7a1833cd373ce15Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-700de64c73c8493eb7a1833cd373ce15Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of N,N-dimethylbenzenesulfonamide (9.25 g; 50 mmol) in dry Et2O (150 ml) under N2 was cooled to −70° C. and added a solution of 2.5 M n-BuLi in hexane (24 ml; 60 mmol) such that the reaction temperature was kept below −60° C. The cooling bath was removed and the reaction mixture allowed to slowly warm up to +20° C. The reaction mixture was re-cooled to −70° C. and B(Oi-Pr)3 (16.1 ml; 70 mmol) was added. The reaction mixture was left cold and allowed to warm up over night, 1 M HCl (100 ml) was added and stirring was continued at rt. for 1 h. The reaction mixture was then extracted with Et2O (2×50 ml) and the combined organic fractions extracted with 1 M NaOH (4×50 ml). The combined aqueous fractions were neutralized with 1 M HCl and extracted with Et2O (4×100 ml). The combined organic fractions were dried (Na2SO4) and evaporated to dryness, washed with Et2O/hexane to give 3.4 g (30%) product. was kept below −60° C The cooling bath was removed to slowly warm up to +20° C The reaction mixture was left cold to warm up over night was continued at rt The reaction mixture was then extracted with Et2O (2×50 ml) the combined organic fractions extracted with 1 M NaOH (4×50 ml) extracted with Et2O (4×100 ml) The combined organic fractions were dried (Na2SO4) evaporated to dryness washed with Et2O/hexane
Source ID: ord-ab55ef4c5f0648e386efeebe3c649426Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of N,N-dimethylbenzenesulfonamide (9.25 g; 50 mmol) in dry Et2O (150 ml) under N2 was cooled to −70° C. and added a solution of 2.5 M n-BuLi in hexane (24 ml; 60 mmol) such that the reaction temperature was kept below −60° C. The cooling bath was removed and the reaction mixture allowed to slowly warm up to +20° C. The reaction mixture was re-cooled to −70° C. and B(Oi-Pr)3 (16.1 ml; 70 mmol) was added. The reaction mixture was left cold and allowed to warm up over night, 1 M HCl (100 ml) was added and stirring was continued at rt. for 1 h. The reaction mixture was then extracted with Et2O (2×50 ml) and the combined organic fractions extracted with 1 M NaOH (4×50 ml). The combined aqueous fractions were neutralized with 1 M HCl and extracted with Et2O (4×100 ml). The combined organic fractions were dried (Na2SO4) and evaporated to dryness, washed with Et2O/hexane to give 3.4 g (30%) product. was kept below −60° C The cooling bath was removed to slowly warm up to +20° C The reaction mixture was left cold to warm up over night was continued at rt The reaction mixture was then extracted with Et2O (2×50 ml) the combined organic fractions extracted with 1 M NaOH (4×50 ml) extracted with Et2O (4×100 ml) The combined organic fractions were dried (Na2SO4) evaporated to dryness washed with Et2O/hexane
Source ID: ord-ab55ef4c5f0648e386efeebe3c649426Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of benzenesulfonylchloride (10 ml; 78 mmol) in THF (100 ml) was added a 40% solution of dimethylamine in H2O (20 ml; 160 mmol) such that the reaction temperature was kept below 50° C. The reaction mixture was stirred 1 h at rt. The reaction mixture was added H2O and THF removed by evaporation. The precipitate formed was isolated by filtration and air dried to give 14 g (97%) of N,N-dimethylbenzenesulfonamide. was kept below 50° C removed by evaporation The precipitate formed was isolated by filtration and air dried
Source ID: ord-da39b0151f124002b1de836bfae7619fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of phenylsulfonyl chloride (10 mL, 78 mmol) in THF (50 mL) was cooled to 0° C. and treated dropwise with dimethylamine (20 mL) as a 40% solution in water maintaining a temperature below 50° C. The reaction was warmed to room temperature for one hour and poured into water. The solution was concentrated to remove THF and the residue was cooled to 0° C. The resulting solid was filtered and dried in vacuo to afford 83A (14 g, 97%). The solution was concentrated to remove THF the residue was cooled to 0° C The resulting solid was filtered dried in vacuo
Source ID: ord-a061b6f8f784428e96a83a22e388c41dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of phenylsulfonyl chloride (10 mL, 78 mmol) in THF (50 mL) was cooled to 0° C. and treated dropwise with dimethylamine (20 mL) as a 40% solution in water maintaining a temperature below 50° C. The reaction was warmed to room temperature for one hour and poured into water. The solution was concentrated to remove THF and the residue was cooled to 0° C. The resulting solid was filtered and dried in vacuo to afford 83A (14 g, 97%). The solution was concentrated to remove THF the residue was cooled to 0° C The resulting solid was filtered dried in vacuo
Source ID: ord-a061b6f8f784428e96a83a22e388c41dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of phenylsulfonyl chloride (10 mL, 78 mmol) in THF (50 mL) was cooled to 0° C. and treated dropwise with dimethylamine (20 mL) as a 40% solution in water maintaining a temperature below 50° C. The reaction was warmed to room temperature for one hour and poured into water. The solution was concentrated to remove THF and the residue was cooled to 0° C. The resulting solid was filtered and dried in vacuo to afford 83A (14 g, 97%). The solution was concentrated to remove THF the residue was cooled to 0° C The resulting solid was filtered dried in vacuo
Source ID: ord-a061b6f8f784428e96a83a22e388c41dConditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of N,N-dimethylbenzenesulfonamide (9.25 g; 50 mmol) in dry Et2O (150 ml) under N2 was cooled to −70° C. and added a solution of 2.5 M n-BuLi in hexane (24 ml; 60 mmol) such that the reaction temperature was kept below −60° C. The cooling bath was removed and the reaction mixture allowed to slowly warm up to +20° C. The reaction mixture was re-cooled to −70° C. and B(Oi-Pr)3 (16.1 ml; 70 mmol) was added. The reaction mixture was left cold and allowed to warm up over night, 1 M HCl (100 ml) was added and stirring was continued at rt. for 1 h. The reaction mixture was then extracted with Et2O (2×50 ml) and the combined organic fractions extracted with 1 M NaOH (4×50 ml). The combined aqueous fractions were neutralized with 1 M HCl and extracted with Et2O (4×100 ml). The combined organic fractions were dried (Na2SO4) and evaporated to dryness, washed with Et2O/hexane to give 3.4 g (30%) product. was kept below −60° C The cooling bath was removed to slowly warm up to +20° C The reaction mixture was left cold to warm up over night was continued at rt The reaction mixture was then extracted with Et2O (2×50 ml) the combined organic fractions extracted with 1 M NaOH (4×50 ml) extracted with Et2O (4×100 ml) The combined organic fractions were dried (Na2SO4) evaporated to dryness washed with Et2O/hexane
Source ID: ord-8ea65a99d7f74ecb9f407694ee52ef25Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of benzenesulfonylchloride (10 ml; 78 mmol) in THF (100 ml) was added a 40% solution of dimethylamine in H2O (20 ml; 160 mmol) such that the reaction temperature was kept below 50° C. The reaction mixture was stirred 1 h at rt. The reaction mixture was added H2O and THF removed by evaporation. The precipitate formed was isolated by filtration and air dried to give 14 g (97%) of N,N-dimethylbenzenesulfonamide. was kept below 50° C removed by evaporation The precipitate formed was isolated by filtration and air dried
Source ID: ord-167d462daca34ec2a30e9a8fc776f5acConditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of N,N-dimethylbenzenesulfonamide (9.25 g; 50 mmol) in dry Et2O (150 ml) under N2 was cooled to −70° C. and added a solution of 2.5 M n-BuLi in hexane (24 ml; 60 mmol) such that the reaction temperature was kept below −60° C. The cooling bath was removed and the reaction mixture allowed to slowly warm up to +20° C. The reaction mixture was re-cooled to −70° C. and B(Oi-Pr)3 (16.1 ml; 70 mmol) was added. The reaction mixture was left cold and allowed to warm up over night, 1 M HCl (100 ml) was added and stirring was continued at rt. for 1 h. The reaction mixture was then extracted with Et2O (2×50 ml) and the combined organic fractions extracted with 1 M NaOH (4×50 ml). The combined aqueous fractions were neutralized with 1 M HCl and extracted with Et2O (4×100 ml). The combined organic fractions were dried (Na2SO4) and evaporated to dryness, washed with Et2O/hexane to give 3.4 g (30%) product. was kept below −60° C The cooling bath was removed to slowly warm up to +20° C The reaction mixture was left cold to warm up over night was continued at rt The reaction mixture was then extracted with Et2O (2×50 ml) the combined organic fractions extracted with 1 M NaOH (4×50 ml) extracted with Et2O (4×100 ml) The combined organic fractions were dried (Na2SO4) evaporated to dryness washed with Et2O/hexane
Source ID: ord-ab55ef4c5f0648e386efeebe3c649426Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of benzenesulfonylchloride (10 ml; 78 mmol) in THF (100 ml) was added a 40% solution of dimethylamine in H2O (20 ml; 160 mmol) such that the reaction temperature was kept below 50° C. The reaction mixture was stirred 1 h at rt. The reaction mixture was added H2O and THF removed by evaporation. The precipitate formed was isolated by filtration and air dried to give 14 g (97%) of N,N-dimethylbenzenesulfonamide. was kept below 50° C removed by evaporation The precipitate formed was isolated by filtration and air dried
Source ID: ord-da39b0151f124002b1de836bfae7619fPubChem References
These sources are listed in the compound's public database record.
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