Thionyl Chloride → HCID 86616005, compound

HRID 1987579Notes

Reaction equation

HRID 1987579 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](O)(=[O:10])=[O:9])=[CH:4][C:3]=1[S:12][CH3:13].S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([Cl:16])(=[O:10])=[O:9])=[CH:4][C:3]=1[S:12][CH3:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86616004HCID 86616004, compound

Product 1

HCID 86616005HCID 86616005, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 4-chloro-3-methylsulfanyl-benzenesulfonic acid (24 mmol) in anhydrous toluene (100 mL) at 0° C. was added thionyl chloride (2.62 mL, 36 mmol). The ice bath was removed and the reaction heated to 85° C. for 5 h, then 70° C. for 18 h. Unreacted starting material was still present by LC-MS and thionyl chloride (5 mL) was added and the reaction stirred for 18 hours at 70° C. The solvent was removed to give a black oil (470 mg, 8%) that was used as is in the next reaction.

Workup

  1. customThe ice bath was removed
  2. additionwas added
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-0905ec078e524623b5e5158509cf6212
Source dataset
uspto-grants-2009_06
Patent number
US07550629B2

Reaction notes

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