No renderable structure data available
C1CN(S(=O)(=O)C1)CC2=CC=C(C=C2)BrChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-[(4-bromophenyl)methyl]-1,2-thiazolidine 1,1-dioxide |
|---|---|
| IUPAC Name | — |
| CAS Number | 950785-37-2 |
| Database ID | 47176171 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-[(4-bromophenyl)methyl]-1,2-thiazolidine 1,1-dioxide (CAS 950785-37-2) 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 47176171
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
10 reactions · 10 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-dbd705babfa241238a7115aa8d3b48ffConditions: temp:190.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2-[(4-bromophenyl)methyl]isothiazolidine 1,1-dioxide (290 mg, 1.0 mmol), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (190 mg, 1.0 mmol), N,N-dimethylglycine (20 mol %, 21 mg, 0.2 mmol), copper (I) iodide (10 mol %, 19 mg, 0.1 mmol) and potassium carbonate (2 mmol, 276 mg) in dimethylsulfoxide (4 ml) was stirred at 190° C. in a microwave reactor for 30 minutes. The reaction mix was partitioned between dichloromethane (5 ml) and water (5 ml). The organic layer was added to a 5 g isolute silica sep-pak column and eluted with ethyl acetate. The solvent was removed under reduced pressure and the residue purified by mass directed auto-prep (MDAP) to give a greasy product which was partitioned between water and dichloromethane. The organic layer was dried over sodium sulphate and evaporated in air to give the title compound as a yellow oil (103 mg, 26%). The reaction mix was partitioned between dichloromethane (5 ml) and water (5 ml) The organic layer was added to a 5 g isolute silica sep-pak column eluted with ethyl acetate The solvent was removed under reduced pressure the residue purified by mass to give a greasy product which was partitioned between water and dichloromethane The organic layer was dried over sodium sulphate evaporated in air
Source ID: ord-182da43cf540491abdfb28c336cab52eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 4-bromobenzylamine (1.85 g, 10 mmol) and triethylamine (2 g, 20 mmol) in dimethylformamide (30 ml) was treated with 3-chloropropanesulfonyl chloride (1.78 g, 10 mmol) by dropwise addition over 10 minutes with stirring under argon. This mix was stirred for 30 minutes before being treated with a 60% suspension of sodium hydride in mineral oil (1.2 g, 30 mmol of NaH) portionwise and the whole mix stirred at room temperature for 3 days. The reaction mixture was partitioned between water (50 ml) and dichloromethane (30 ml). The organic layer was dried over sodium sulphate and reduced to minimum volume by rotary evaporation. The residue was added to a 20 g pre-packed silica column and eluted from 0-50% ethyl acetate in petroleum ether to give the title compound as a yellow oil (2.72 g, 94%). This mix was stirred for 30 minutes the whole mix stirred at room temperature for 3 days The reaction mixture was partitioned between water (50 ml) and dichloromethane (30 ml) The organic layer was dried over sodium sulphate reduced to minimum volume by rotary evaporation The residue was added to a 20 g pre-packed silica column eluted from 0-50% ethyl acetate in petroleum ether
Source ID: ord-db11cd52a348417299c12d8ed0030cd4Conditions: temp:190.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2-[(4-bromophenyl)methyl]isothiazolidine 1,1-dioxide (290 mg, 1.0 mmol), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (190 mg, 1.0 mmol), N,N-dimethylglycine (20 mol %, 21 mg, 0.2 mmol), copper (I) iodide (10 mol %, 19 mg, 0.1 mmol) and potassium carbonate (2 mmol, 276 mg) in dimethylsulfoxide (4 ml) was stirred at 190° C. in a microwave reactor for 30 minutes. The reaction mix was partitioned between dichloromethane (5 ml) and water (5 ml). The organic layer was added to a 5 g isolute silica sep-pak column and eluted with ethyl acetate. The solvent was removed under reduced pressure and the residue purified by mass directed auto-prep (MDAP) to give a greasy product which was partitioned between water and dichloromethane. The organic layer was dried over sodium sulphate and evaporated in air to give the title compound as a yellow oil (103 mg, 26%). The reaction mix was partitioned between dichloromethane (5 ml) and water (5 ml) The organic layer was added to a 5 g isolute silica sep-pak column eluted with ethyl acetate The solvent was removed under reduced pressure the residue purified by mass to give a greasy product which was partitioned between water and dichloromethane The organic layer was dried over sodium sulphate evaporated in air
Source ID: ord-182da43cf540491abdfb28c336cab52eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 4-bromobenzylamine (1.85 g, 10 mmol) and triethylamine (2 g, 20 mmol) in dimethylformamide (30 ml) was treated with 3-chloropropanesulfonyl chloride (1.78 g, 10 mmol) by dropwise addition over 10 minutes with stirring under argon. This mix was stirred for 30 minutes before being treated with a 60% suspension of sodium hydride in mineral oil (1.2 g, 30 mmol of NaH) portionwise and the whole mix stirred at room temperature for 3 days. The reaction mixture was partitioned between water (50 ml) and dichloromethane (30 ml). The organic layer was dried over sodium sulphate and reduced to minimum volume by rotary evaporation. The residue was added to a 20 g pre-packed silica column and eluted from 0-50% ethyl acetate in petroleum ether to give the title compound as a yellow oil (2.72 g, 94%). This mix was stirred for 30 minutes the whole mix stirred at room temperature for 3 days The reaction mixture was partitioned between water (50 ml) and dichloromethane (30 ml) The organic layer was dried over sodium sulphate reduced to minimum volume by rotary evaporation The residue was added to a 20 g pre-packed silica column eluted from 0-50% ethyl acetate in petroleum ether
Source ID: ord-db11cd52a348417299c12d8ed0030cd4Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-dbd705babfa241238a7115aa8d3b48ffConditions: temp:190.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2-[(4-bromophenyl)methyl]isothiazolidine 1,1-dioxide (290 mg, 1.0 mmol), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (190 mg, 1.0 mmol), N,N-dimethylglycine (20 mol %, 21 mg, 0.2 mmol), copper (I) iodide (10 mol %, 19 mg, 0.1 mmol) and potassium carbonate (2 mmol, 276 mg) in dimethylsulfoxide (4 ml) was stirred at 190° C. in a microwave reactor for 30 minutes. The reaction mix was partitioned between dichloromethane (5 ml) and water (5 ml). The organic layer was added to a 5 g isolute silica sep-pak column and eluted with ethyl acetate. The solvent was removed under reduced pressure and the residue purified by mass directed auto-prep (MDAP) to give a greasy product which was partitioned between water and dichloromethane. The organic layer was dried over sodium sulphate and evaporated in air to give the title compound as a yellow oil (103 mg, 26%). The reaction mix was partitioned between dichloromethane (5 ml) and water (5 ml) The organic layer was added to a 5 g isolute silica sep-pak column eluted with ethyl acetate The solvent was removed under reduced pressure the residue purified by mass to give a greasy product which was partitioned between water and dichloromethane The organic layer was dried over sodium sulphate evaporated in air
Source ID: ord-ddde6c5d64dd4217bb74766c398db1abConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 4-bromobenzylamine (1.85 g, 10 mmol) and triethylamine (2 g, 20 mmol) in dimethylformamide (30 ml) was treated with 3-chloropropanesulfonyl chloride (1.78 g, 10 mmol) by dropwise addition over 10 minutes with stirring under argon. This mix was stirred for 30 minutes before being treated with a 60% suspension of sodium hydride in mineral oil (1.2 g, 30 mmol of NaH) portionwise and the whole mix stirred at room temperature for 3 days. The reaction mixture was partitioned between water (50 ml) and dichloromethane (30 ml). The organic layer was dried over sodium sulphate and reduced to minimum volume by rotary evaporation. The residue was added to a 20 g pre-packed silica column and eluted from 0-50% ethyl acetate in petroleum ether to give the title compound as a yellow oil (2.72 g, 94%). This mix was stirred for 30 minutes the whole mix stirred at room temperature for 3 days The reaction mixture was partitioned between water (50 ml) and dichloromethane (30 ml) The organic layer was dried over sodium sulphate reduced to minimum volume by rotary evaporation The residue was added to a 20 g pre-packed silica column eluted from 0-50% ethyl acetate in petroleum ether
Source ID: ord-fc7c0eecd520456cacbb1ee0086daca7Conditions: temp:190.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2-[(4-bromophenyl)methyl]isothiazolidine 1,1-dioxide (290 mg, 1.0 mmol), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (190 mg, 1.0 mmol), N,N-dimethylglycine (20 mol %, 21 mg, 0.2 mmol), copper (I) iodide (10 mol %, 19 mg, 0.1 mmol) and potassium carbonate (2 mmol, 276 mg) in dimethylsulfoxide (4 ml) was stirred at 190° C. in a microwave reactor for 30 minutes. The reaction mix was partitioned between dichloromethane (5 ml) and water (5 ml). The organic layer was added to a 5 g isolute silica sep-pak column and eluted with ethyl acetate. The solvent was removed under reduced pressure and the residue purified by mass directed auto-prep (MDAP) to give a greasy product which was partitioned between water and dichloromethane. The organic layer was dried over sodium sulphate and evaporated in air to give the title compound as a yellow oil (103 mg, 26%). The reaction mix was partitioned between dichloromethane (5 ml) and water (5 ml) The organic layer was added to a 5 g isolute silica sep-pak column eluted with ethyl acetate The solvent was removed under reduced pressure the residue purified by mass to give a greasy product which was partitioned between water and dichloromethane The organic layer was dried over sodium sulphate evaporated in air
Source ID: ord-182da43cf540491abdfb28c336cab52eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 4-bromobenzylamine (1.85 g, 10 mmol) and triethylamine (2 g, 20 mmol) in dimethylformamide (30 ml) was treated with 3-chloropropanesulfonyl chloride (1.78 g, 10 mmol) by dropwise addition over 10 minutes with stirring under argon. This mix was stirred for 30 minutes before being treated with a 60% suspension of sodium hydride in mineral oil (1.2 g, 30 mmol of NaH) portionwise and the whole mix stirred at room temperature for 3 days. The reaction mixture was partitioned between water (50 ml) and dichloromethane (30 ml). The organic layer was dried over sodium sulphate and reduced to minimum volume by rotary evaporation. The residue was added to a 20 g pre-packed silica column and eluted from 0-50% ethyl acetate in petroleum ether to give the title compound as a yellow oil (2.72 g, 94%). This mix was stirred for 30 minutes the whole mix stirred at room temperature for 3 days The reaction mixture was partitioned between water (50 ml) and dichloromethane (30 ml) The organic layer was dried over sodium sulphate reduced to minimum volume by rotary evaporation The residue was added to a 20 g pre-packed silica column eluted from 0-50% ethyl acetate in petroleum ether
Source ID: ord-db11cd52a348417299c12d8ed0030cd4PubChem References
These sources are listed in the compound's public database record.
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