m-Chloroperbenzoic acid → HCID 53818564, compound

HRID 460772Notes

Reaction equation

HRID 460772 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:7][S:6](=[O:9])(=[O:8])[CH2:5][C:4]([CH3:11])([CH3:10])[NH:3]1.ClC1C=C(C=CC=1)C(OO)=[O:18]>C(Cl)Cl>[CH3:1][C:2]1([CH3:12])[CH2:7][S:6](=[O:9])(=[O:8])[CH2:5][C:4]([CH3:11])([CH3:10])[NH+:3]1[O-:18]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21394477HCID 21394477, compound

Product 1

HCID 53818564HCID 53818564, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5.7 g (0.03 mole) of 2,2,6,6-tetramethyl-1-aza-4-thiacyclohexane-4,4-dioxide is dissolved in 100 ml of methylene chloride. To this solution there is then added dropwise at 20° C in ca. 90 minutes a solution of 11.2 g of m-chloroperoxybenzoic acid in 100 ml of methylene chloride. The reaction is slightly exothermic. Stirring is subsequently maintained for 15 hours at room temperature, and the precipitated m-chlorobenzoic acid filtered off. The reddish coloured methylene chloride solution is extracted twice with 50 ml of 2N sodium hydroxide solution each time, and then with 50 ml of 2N hydrochloric acid, and subsequently dried over sodium sulphate. After the solvent has been distilled off, the residue is crystallised from ethanol to obtain 2,2,6,6-tetramethyl-1-aza-4-thiacyclohexane-1,4,4-trioxide (8) of the formula ##STR19## M.P. 163° C.

Workup

  1. filtrationthe precipitated m-chlorobenzoic acid filtered off
  2. extractionThe reddish coloured methylene chloride solution is extracted twice with 50 ml of 2N sodium hydroxide solution each time
  3. dry with materialwith 50 ml of 2N hydrochloric acid, and subsequently dried over sodium sulphate
  4. distillationAfter the solvent has been distilled off
  5. customthe residue is crystallised from ethanol

Sources & evidence

ORD record
ord-3d16f8c27ec24151b3621d490160021a
Source dataset
uspto-grants-1977_12
Patent number
US04061631

Reaction notes

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