3-Chlorobenzoic Acid → 5-Benzenesulfinyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole

HRID 1198368Notes

Reaction equation

HRID 1198368 reaction equation
[C:1]1([S:7][C:8]2[CH:31]=[CH:30][C:11]3=[N:12][N:13]([C:15]4[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=[C:17]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:16]=4[OH:29])[N:14]=[C:10]3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:37].ClC1C=C(C=CC=1)C(O)=O>C(Cl)Cl>[C:1]1([S:7]([C:8]2[CH:31]=[CH:30][C:11]3=[N:12][N:13]([C:15]4[CH:20]=[C:19]([C:21]([CH3:24])([CH3:22])[CH3:23])[CH:18]=[C:17]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:16]=4[OH:29])[N:14]=[C:10]3[CH:9]=2)=[O:37])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 4473-Chlorobenzoic AcidHCID 70297m-Chloroperbenzoic acidHCID 193491505-Phenylthio-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole

Product 1

HCID 193491565-Benzenesulfinyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazoleYield 87.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 10.8 g (0.025 mole) of 5-phenylthio-2-(2-hydroxy-3,5-di-tert-butyl-phenyl)-2H-benzotriazole, prepared in Example 2, in 80 mL of methylene chloride is cooled to 3°-5° C. Over a period of 30 min. is added a solution of 5.1 g (0.025 mole) of m-chloroperoxybenzoic acid (MCPBA) 85% in 80 mL of methylene chloride at 3°-5° C. The reaction is stirred for 2 hours at 0°-5° C. with precipitation of m-chlorobenzoic acid. The starting material is shown to be absent. Upon removal of the solvent the residue is dissolved in 200 mL of toluene, m-chlorobenzoic acid is removed by filtration and subsequent washing with 10% aqueous sodium carbonate solution and water. The toluene solution is dried over anhydrous magnesium sulfate, filtered and the solvent removed. The resulting amorphous residue is dissolved in 60 mL of petroleum ether and crystallized. Filtration and washing of the crystals with cold petroleum ether affords 9.8 g (87.6% yield) of the title compound as a solid melting at 152°-154° C.

Workup

  1. temperatureis cooled to 3°-5° C
  2. customUpon removal of the solvent the residue
  3. dissolutionis dissolved in 200 mL of toluene
  4. customm-chlorobenzoic acid is removed by filtration
  5. washsubsequent washing with 10% aqueous sodium carbonate solution and water
  6. dry with materialThe toluene solution is dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent removed
  9. dissolutionThe resulting amorphous residue is dissolved in 60 mL of petroleum ether
  10. customcrystallized
  11. filtrationFiltration
  12. washwashing of the crystals with cold petroleum ether

Sources & evidence

ORD record
ord-051106cc214746e6a207e27f439f3883
Source dataset
uspto-grants-1994_01
Patent number
US05280124

Reaction notes

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