No renderable structure data available
CS(=O)(=O)NCCC1=CC=CC=C1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | N-(2-phenylethyl)methanesulfonamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 33893-36-6 |
| Database ID | 118569 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
N-(2-phenylethyl)methanesulfonamide (CAS 33893-36-6) 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 118569
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-d0182f79d97d4afdb0d121e7ea98fc9aConditions: temp:72.51; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirring room temperature solution of N-(methylsulfonyl)-N-(2-phenylethyl)amine (205 g, 1.03 moles), water (200 mL), 95% sulfuric acid (111 g, 1.08 moles) in acetic acid (1 L), was added iodine (111 g, 0.438 mol) and periodic acid (45.6 g, 0.206 mol). The reaction mixture was warmed to 70-75° C. for 3 h. The heat was removed and the dark violet reaction mixture was allowed to proceed overnight at room temperature. Potassium hydroxide pellets (85%, 143 g, 2.16 moles) were added to neutralized the sulfuric acid and then enough saturated aqueous sodium sulfite was added to decolorize the mixture to afford a white suspension. The suspension was cooled to 15° C. and filtered. The filter cake was triturated thoroughly with water and was then dissolved in CH2Cl2 (1 L) and extracted with additional water (2×200 mL). The organic phase was concentrated under reduced pressure to provide N-(2-(4-iodophenyl)ethyl)-N-(methylsulfonyl)amine, (201 g, 60.2%) as a white powder. 1H NMR (300 MHz) 7.64 (d, 2H, J=4.8), 6.97 (d, 2H, J=5.1), 4.37 (br t, 1H, J=4), 3.36 (app. q, 2H, J=3.9), 2.85 (s, 3H), 2.82 (t, 2H, J=3.9). The heat was removed were added enough saturated aqueous sodium sulfite was added to afford a white suspension The suspension was cooled to 15° C. filtered The filter cake was triturated thoroughly with water was then dissolved in CH2Cl2 (1 L) extracted with additional water (2×200 mL) The organic phase was concentrated under reduced pressure
Source ID: ord-7f2f12d4bb5b43829551c2e6f509749fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 10° C. solution of phenethylamine (12.1 g, 0.100 mol) and triethylamine (11.1 g, 0.110 mol) in CH2Cl2 (50 mL) was added methanesulfonyl chloride (12.6 g, 0.110 mol) dropwise over 10 min. The solution was stirred at room temperature for 1.5 h and was then washed with 1 N HCl (5×20 mL). The organic phase was directly concentrated to provide the intermediate title compound, N-(methylsulfonyl)(2-phenylethyl)amine, (21.2 g, 93.3%) as an oil. 1H NMR (300 MHz) 7.32 (m, 2H), 7.23 (m, 3H), 4.30 (br s, 1H), 3.40 (t, 2H, J=3.9), 2.88 (t, 2H, J=4.2), 2.81 (s, 3H). was then washed with 1 N HCl (5×20 mL) The organic phase was directly concentrated
Source ID: ord-a1b43f693aff48dc9d6cd293b2175760Conditions: temp:72.51; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirring room temperature solution of N-(methylsulfonyl)-N-(2-phenylethyl)amine (205 g, 1.03 moles), water (200 mL), 95% sulfuric acid (111 g, 1.08 moles) in acetic acid (1 L), was added iodine (111 g, 0.438 mol) and periodic acid (45.6 g, 0.206 mol). The reaction mixture was warmed to 70-75° C. for 3 h. The heat was removed and the dark violet reaction mixture was allowed to proceed overnight at room temperature. Potassium hydroxide pellets (85%, 143 g, 2.16 moles) were added to neutralized the sulfuric acid and then enough saturated aqueous sodium sulfite was added to decolorize the mixture to afford a white suspension. The suspension was cooled to 15° C. and filtered. The filter cake was triturated thoroughly with water and was then dissolved in CH2Cl2 (1 L) and extracted with additional water (2×200 mL). The organic phase was concentrated under reduced pressure to provide N-(2-(4-iodophenyl)ethyl)-N-(methylsulfonyl)amine, (201 g, 60.2%) as a white powder. 1H NMR (300 MHz) 7.64 (d, 2H, J=4.8), 6.97 (d, 2H, J=5.1), 4.37 (br t, 1H, J=4), 3.36 (app. q, 2H, J=3.9), 2.85 (s, 3H), 2.82 (t, 2H, J=3.9). The heat was removed were added enough saturated aqueous sodium sulfite was added to afford a white suspension The suspension was cooled to 15° C. filtered The filter cake was triturated thoroughly with water was then dissolved in CH2Cl2 (1 L) extracted with additional water (2×200 mL) The organic phase was concentrated under reduced pressure
Source ID: ord-7f2f12d4bb5b43829551c2e6f509749fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 10° C. solution of phenethylamine (12.1 g, 0.100 mol) and triethylamine (11.1 g, 0.110 mol) in CH2Cl2 (50 mL) was added methanesulfonyl chloride (12.6 g, 0.110 mol) dropwise over 10 min. The solution was stirred at room temperature for 1.5 h and was then washed with 1 N HCl (5×20 mL). The organic phase was directly concentrated to provide the intermediate title compound, N-(methylsulfonyl)(2-phenylethyl)amine, (21.2 g, 93.3%) as an oil. 1H NMR (300 MHz) 7.32 (m, 2H), 7.23 (m, 3H), 4.30 (br s, 1H), 3.40 (t, 2H, J=3.9), 2.88 (t, 2H, J=4.2), 2.81 (s, 3H). was then washed with 1 N HCl (5×20 mL) The organic phase was directly concentrated
Source ID: ord-a1b43f693aff48dc9d6cd293b2175760Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 10° C. solution of phenethylamine (12.1 g, 0.100 mol) and triethylamine (11.1 g, 0.110 mol) in CH2Cl2 (50 mL) was added methanesulfonyl chloride (12.6 g, 0.110 mol) dropwise over 10 min. The solution was stirred at room temperature for 1.5 h and was then washed with 1 N HCl (5×20 mL). The organic phase was directly concentrated to provide the intermediate title compound, N-(methylsulfonyl)(2-phenylethyl)amine, (21.2 g, 93.3%) as an oil. 1H NMR (300 MHz) 7.32 (m, 2H), 7.23 (m, 3H), 4.30 (br s, 1H), 3.40 (t, 2H, J=3.9), 2.88 (t, 2H, J=4.2), 2.81 (s, 3H). was then washed with 1 N HCl (5×20 mL) The organic phase was directly concentrated
Source ID: ord-a1b43f693aff48dc9d6cd293b2175760Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d0182f79d97d4afdb0d121e7ea98fc9aConditions: temp:72.51; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirring room temperature solution of (methylsulfonyl)(2-phenylethyl)amine (205 g, 1.03 moles), water (200 mL), 95% sulfuric acid (111 g, 1.08 moles) in acetic acid (1 L), was added iodine (111 g, 0.438 mol) and periodic acid (H5IO6, 45.6 g, 0.206 mol). The reaction mixture was warmed to 70-75° C. for 3 h. The heat was removed and the dark violet reaction mixture was allowed to proceed overnight at room temperature. Potassium hydroxide pellets (85%, 143 g, 2.16 moles) were added to neutralized the sulfuric acid and then enough saturated aqueous sodium sulfite was added to decolorize the mixture to afford a white suspension. The suspension was cooled to 15° C. and filtered. The filter cake was triturated thoroughly with water and was then dissolved in CH2Cl2 (1 L) and extracted with additional water (2×200 mL). The organic phase was concentrated under reduced pressure to provide the intermediate title compound, [2-(4-iodophenyl)ethyl](methylsulfonyl)amine, (201 g, 60.2%) as a white powder. 1H NMR (CDCl3, 300 MHz) δ 7.64 (d, 2H, J=4.8), 6.97 (d, 2H, J=5.1), 4.37 (br t, 1H, J=4), 3.36 (app. q, 2H, J=3.9), 2.85 (s, 3H), 2.82 (t, 2H, J=3.9). The heat was removed were added enough saturated aqueous sodium sulfite was added to afford a white suspension The suspension was cooled to 15° C. filtered The filter cake was triturated thoroughly with water was then dissolved in CH2Cl2 (1 L) extracted with additional water (2×200 mL) The organic phase was concentrated under reduced pressure
Source ID: ord-484618be100045618a47e1edd5d7d15bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 10° C. solution of phenethylamine (12.1 g, 0.100 mol) and triethylamine (11.1 g, 0.110 mol) in CH2Cl2 (50 mL) was added methanesulfonyl chloride (12.6 g, 0.110 mol) dropwise over 10 min. The solution was stirred at room temperature for 1.5 h and was then washed with 1 N HCl (5×20 mL). The organic phase was directly concentrated to provide the intermediate title compound, (methylsulfonyl)(2-phenylethyl)amine, (21.2 g, 93.3%) as an oil. 1H NMR (CDCl3, 300 MHz) δ7.32 (m, 2H), 7.23 (m, 3H), 4.30 (br s, 1H), 3.40 (t, 2H, J=3.9), 2.88 (t, 2H, J=4.2), 2.81 (s, 3H). was then washed with 1 N HCl (5×20 mL) The organic phase was directly concentrated
Source ID: ord-bdf136999f624cacb9a8ddf4ed3495fdConditions: temp:72.51; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirring room temperature solution of (methylsulfonyl)(2-phenylethyl)amine (205 g, 1.03 moles), water (200 mL), 95% sulfuric acid (111 g, 1.08 moles) in acetic acid (1 L), was added iodine (111 g, 0.438 mol) and periodic acid (H5lO6, 45.6 g, 0.206 mol). The reaction mixture was warmed to 70-75° C. for 3 h. The heat was removed and the dark violet reaction mixture was allowed to proceed overnight at room temperature. Potassium hydroxide pellets (85%, 143 g, 2.16 moles) were added to neutralized the sulfuric acid and then enough saturated aqueous sodium sulfite was added to decolorize the mixture to afford a white suspension. The suspension was cooled to 15° C. and filtered. The filter cake was triturated thoroughly with water and was then dissolved in CH2Cl2 (1 L) and extracted with additional water (2×200 mL). The organic phase was concentrated under reduced pressure to provide the intermediate title compound, [2-(4-iodophenyl)ethyl](methylsulfonyl)amine, (201 g, 60.2%) as a white powder. The heat was removed were added enough saturated aqueous sodium sulfite was added to afford a white suspension The suspension was cooled to 15° C. filtered The filter cake was triturated thoroughly with water was then dissolved in CH2Cl2 (1 L) extracted with additional water (2×200 mL) The organic phase was concentrated under reduced pressure
Source ID: ord-d17ef85d94fb42acb1b94f03aee15270Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 10° C. solution of phenethylamine (12.1 g, 0.100 mol) and triethylamine (11.1 g, 0.110 mol) in CH2Cl2 (50 mL) was added methanesulfonyl chloride (12.6 g, 0.110 mol) dropwise over 10 min. The solution was stirred at room temperature for 1.5 h and was then washed with 1N HCl (5×20 mL). The organic phase was directly concentrated to provide the intermediate title compound, (methylsulfonyl)(2-phenylethyl)amine, (21.2 g, 93.3%) as an oil. was then washed with 1N HCl (5×20 mL) The organic phase was directly concentrated
Source ID: ord-f41c03bc4a954803a615241c2fef61deConditions: temp:72.51; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirring room temperature solution of N-(methylsulfonyl)-N-(2-phenylethyl)amine (205 g, 1.03 moles), water (200 mL), 95% sulfuric acid (111 g, 1.08 moles) in acetic acid (1 L), was added iodine (111 g, 0.438 mol) and periodic acid (45.6 g, 0.206 mol). The reaction mixture was warmed to 70-75° C. for 3 h. The heat was removed and the dark violet reaction mixture was allowed to proceed overnight at room temperature. Potassium hydroxide pellets (85%, 143 g, 2.16 moles) were added to neutralized the sulfuric acid and then enough saturated aqueous sodium sulfite was added to decolorize the mixture to afford a white suspension. The suspension was cooled to 15° C. and filtered. The filter cake was triturated thoroughly with water and was then dissolved in CH2Cl2 (1 L) and extracted with additional water (2×200 mL). The organic phase was concentrated under reduced pressure to provide N-(2-(4-iodophenyl)ethyl)-N-(methylsulfonyl)amine, (201 g, 60.2%) as a white powder. 1H NMR (300 MHz) 7.64 (d, 2H, J=4.8), 6.97 (d, 2H, J=5.1), 4.37 (br t, 1H, J=4), 3.36 (app. q, 2H, J=3.9), 2.85 (s, 3H), 2.82 (t, 2H, J=3.9). The heat was removed were added enough saturated aqueous sodium sulfite was added to afford a white suspension The suspension was cooled to 15° C. filtered The filter cake was triturated thoroughly with water was then dissolved in CH2Cl2 (1 L) extracted with additional water (2×200 mL) The organic phase was concentrated under reduced pressure
Source ID: ord-7f2f12d4bb5b43829551c2e6f509749fPubChem References
These sources are listed in the compound's public database record.
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