Chlorosuccinimide → HCID 14232132, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:17])[N:5]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)[N:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1)[CH3:2].[Cl:18]N1C(=O)CCC1=O.S(=O)(O)[O-].[Na+]>O1CCCC1>[ClH:18].[CH2:1]([O:3][C:4](=[O:17])[N:5]([N:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[Cl:18])[C:11]1[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=1)[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of N-(4-pyridinyl)-N-(1H-pyrrol-1-yl)carbamic acid ethyl ester (9 g) in 100 ml of anhydrous tetrahydrofuran warmed to 50° C. was slowly dropped a solution of N-chlorosuccinimide (5.2 g) in 75 ml of anhydrous tetrahydrofuran. After stirring seven hours at 50° C., the reaction mixture was cooled, stirred with an aqueous solution of sodium bisulfite and extracted with ethyl acetate. The organic extract was washed with water and saturated sodium chloride solution and thereafter dried over anhydrous magnesium sulfate, filtered and evaporated to 11.5 g of an oil. This oil was purified by HPLC (silica, 20% ethyl acetate in dichloromethane) to give 3.8 g of the desired product as a solid. This material was converted to the hydrochloride salt and twice recrystallized from isopropanol-ether to give 3.3 g of crystals, m.p. 139°-140° C. (dec.).
Workup
- temperaturethe reaction mixture was cooled
- extractionextracted with ethyl acetate
- extractionThe organic extract
- washwas washed with water and saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customevaporated to 11.5 g of an oil
- customThis oil was purified by HPLC (silica, 20% ethyl acetate in dichloromethane)
Sources & evidence
- ORD record
- ord-20c1a265787d4218938bbb4bcce9e8a3
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05776955
Reaction notes
Loading…