Chlorosuccinimide → HCID 15704073, compound

HRID 1651517Notes

Reaction equation

HRID 1651517 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]2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 15704064(2,3-Dihydro-1H-indol-7-yl)(2-fluorophenyl)methanone

Product 1

HCID 15704073HCID 15704073, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. customequipped with a central stirrer, a condenser
  2. customprovided with a calcium chloride guard tube
  3. washThe mixture is washed with saturated sodium bicarbonate solution
  4. dry with materialwith water, dried
  5. customevaporated
  6. customIt is chromatographed on silica
  7. washeluting with methylene chloride
  8. custom42 g (84% yield) are obtained
  9. customThe product is obtained in the form of a foam which

Sources & evidence

ORD record
ord-31a62ec14130425ca414cebd4a2f40e4
Source dataset
uspto-grants-1990_05
Patent number
US04929614

Reaction notes

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