Chlorosuccinimide → HCID 15704073, compound
Reaction equation
[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH2:12][CH2:11]2)=[O:5].[Cl:19]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:19][C:8]1[CH:9]=[C:10]2[C:14](=[C:6]([C:4](=[O:5])[C:3]3[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=3[F:1])[CH:7]=1)[NH:13][CH2:12][CH2:11]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
44 g (182 mmol) of 7-(2-fluorobenzoyl)indoline and 800 ml of methylene chloride are poured into a reactor equipped with a central stirrer, a condenser provided with a calcium chloride guard tube, a dipping thermometer, a nitrogen inlet and a pressure-equalizing dropping funnel. 27.9 g (182 mmol) of N-chlorosuccinimide are added gradually and the mixture is stirred over a warm temperature. The mixture is washed with saturated sodium bicarbonate solution and then with water, dried and evaporated. It is chromatographed on silica, eluting with methylene chloride. 42 g (84% yield) are obtained. The product is obtained in the form of a foam which has no definite melting point. TLC: H2CCl2Rf=0.70.