Sulfuric Acid → HCID 69313521, compound
Reaction equation
N([O-])=O.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=C[CH:7]=1.S(=O)(=O)(O)O.[I-:17].[K+].[CH:19]([Cl:22])(Cl)Cl>O>[Cl:22][C:19]1[CH:9]=[CH:10][C:11]([I:17])=[C:6]([N:5]2[CH2:10][CH2:11][CH2:6][CH2:7]2)[CH:7]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
Add a solution of 0.58 g (8.45 mmol) of sodium nitrite in 3 mL of water to a mixture of the aniline (1.66 g, 8.45 mmol), 19 mL of water and 5 mL of concentrated sulfuric acid cooled at 5° C. in an ice bath, while maintaining the temperature below 10° C. Stir the mixture for 30 min and pour the solution into a solution of 1.75 g (10.56 mmol) of potassium iodide in 10 mL of water. Heat the aqueous solution at 60° C. for 3 h. Cool the black solution and add chloroform. Separate the organic layer and wash with 10% sodium hydroxide, 1M sodium thiosulfate, 10% hydrochloric acid, water, saturated sodium bicarbonate and brine. Dry the organic layer over MgSO4, filter, concentrate the solvent under reduced pressure and chromatograph the residue using Hex/EtOAc 98:2 to provide 1-(5-chloro-2-iodo-phenyl)-pyrrolidine (60% yield). From this material, prepare the title compound using a procedure similar to Preparation 1.
Workup
- temperaturewhile maintaining the temperature below 10° C
- temperatureHeat the aqueous solution at 60° C. for 3 h
- temperatureCool the black solution
- customSeparate the organic layer
- washwash with 10% sodium hydroxide, 1M sodium thiosulfate, 10% hydrochloric acid, water, saturated sodium bicarbonate and brine
- dry with materialDry the organic layer over MgSO4
- filtrationfilter
- concentrationconcentrate the solvent under reduced pressure and chromatograph the residue
Sources & evidence
- ORD record
- ord-6042446aa97c4785abb2565a9e1e4e1d
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07449477B2
Reaction notes
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