Chlorosuccinimide → Ethyl 5-chloro-3,3-dimethyl-5-phenylthiopentanoate

HRID 66452Notes

Reaction equation

HRID 66452 reaction equation
[CH3:1][C:2]([CH3:17])([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[S:5].[Cl:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:18][CH:10]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:9][C:2]([CH3:1])([CH3:17])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[S:5]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 53723614Ethyl 3,3-dimethyl-5-phenylthiopentanoate

Product 1

HCID 54461625Ethyl 5-chloro-3,3-dimethyl-5-phenylthiopentanoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1.06 g (3.09 mmol) of ethyl 3,3-dimethyl-5-phenylthiopentanoate in 10 mL of carbon tetrachloride was added 590 mg (4.4 mmol) of 1-chloro-2,5-pyrrolidinedione, and the mixture was stirred at room temperature for 2 hours. The mixture was filtered, and the filtrate concentrated to give ethyl 5-chloro-3,3-dimethyl-5-phenylthiopentanoate as an oil. The product was used without further purification in the reaction described in Example 3 below. NMR Data (CDCl3):

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-1ef41fa1a20f46689290f67358a593e3
Source dataset
uspto-grants-1982_08
Patent number
US04342694

Reaction notes

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