Water → HCID 15380615, compound

HRID 321956Notes

Reaction equation

HRID 321956 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:15]([CH3:16])=[C:14]([Cl:17])[CH:13]=[CH:12][C:11]=1[S:18]([Cl:21])(=[O:20])=[O:19].O>ClC(Cl)C(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][CH2:16][C:15]1[C:10]([Cl:9])=[C:11]([S:18]([Cl:21])(=[O:20])=[O:19])[CH:12]=[CH:13][C:14]=1[Cl:17]

Participants

6

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 157253742,4-Dichloro-3-methylbenzene-1-sulfonyl chloride

Product 1

HCID 15380615HCID 15380615, compoundYield 11.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 65911,1,2,2-TetrachloroethaneSolvent

Conditions

Temperature
120 °C

Procedure

10 g (0.075 mol) of N-chlorosuccinimide and 30 mg of benzoyl peroxide are added to a solution of 6.5 g (0.025 mol) of 2,4-dichloro-3-methylbenzenesulfonyl chloride in 30 ml of 1,1,2,2-tetrachloroethane at room temperature and under a nitrogen atmosphere. The reaction mixture is heated at 120° C. for 3 hours, cooled to room temperature, poured into water and then extracted with dichloromethane. The organic phase is washed with water, with saturated sodium bicarbonate solution and finally with water until the washings are neutral. It is then dried over magnesium sulfate and concentrated under reduced pressure. Recrystallization from hexane gives 0.85 g of the expected product in the form of white crystals (yield=11.5%).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with dichloromethane
  3. washThe organic phase is washed with water, with saturated sodium bicarbonate solution and finally with water until the washings
  4. dry with materialIt is then dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customRecrystallization from hexane

Sources & evidence

ORD record
ord-8f701e0bd2f24123b5898199aa541e08
Source dataset
uspto-grants-2001_04
Patent number
US06211181B1

Reaction notes

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