Water → HCID 15380615, compound

HRID 1421880Notes

Reaction equation

HRID 1421880 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-3b488a3544e643acb9ded9eaf310385a
Source dataset
uspto-grants-2000_06
Patent number
US06080758

Reaction notes

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