Chlorosuccinimide → Chloromethyl p-Tolyl Sulfide

HRID 2199377

Reaction equation

HRID 2199377 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([S:7][CH3:8])=[CH:3][CH:2]=1.[Cl:10]N1C(=O)CCC1=O>ClC1C=CC=CC=1>[Cl:10][CH2:8][S:7][C:4]1[CH:5]=[CH:6][C:1]([CH3:9])=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 69334Benzene, 1-methyl-4-(methylthio)-

Product 1

HCID 1502059Chloromethyl p-Tolyl SulfideYield 109.7%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Methyl p-tolyl sulfide (75 g, 542.27 mmol) was diluted in chorobenzene (452 mL). N-Chloro Succinimide (NCS) (76.07 g, 1.05 eq) was added in small portions maintaining the temperature between 35° C. and 45° C., under an argon atmosphere. The reaction mixture was stirred at the same temperature range until the reaction was complete. After that time, the solution turned into a suspension. The suspension formed was filtered and the solid was washed with chlorobenzene (50 ml). The filtrate was washed with water (3×225 mL). The resulting organic phase was dried with magnesium sulfate and concentrated. The crude product was purified by distillation to give 102.68 g (100%) of the desired product as yellow oil (bp: 96° C. at 40 Pa).

Workup

  1. temperaturemaintaining the temperature between 35° C. and 45° C.
  2. customThe suspension formed
  3. filtrationwas filtered
  4. washthe solid was washed with chlorobenzene (50 ml)
  5. washThe filtrate was washed with water (3×225 mL)
  6. dry with materialThe resulting organic phase was dried with magnesium sulfate
  7. concentrationconcentrated
  8. distillationThe crude product was purified by distillation

Sources & evidence

ORD record
ord-146314b5fd1e4cc696b469254fe898b2
Source dataset
uspto-grants-2016_06
Patent number
US09359294B2

Linked notes

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