m-Chloroperbenzoic acid → HCID 13173176, compound

HRID 980354Notes

Reaction equation

HRID 980354 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[N:17]=[C:18]3[N:22]([CH:23]=2)[CH2:21][CH2:20][S:19]3=[O:24])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[N:17]=[C:18]3[N:22]([CH:23]=2)[CH2:21][CH2:20][S:19]3(=[O:33])=[O:24])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 13173175HCID 13173175, compound

Product 1

HCID 13173176HCID 13173176, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 10 ml of chloroform was dissolved 0.6 g of 6-(3,5-di-tert-butyl-4-hydroxyphenyl)-2,3-dihydroimidazo[2,1-b]thiazole 1-oxide and then 0.4 g of m-chloroperbenzoic acid was added to the solution. After 30 minutes, 0.4 g of m-chloroperbenzoic acid was further added to the mixture and the resultant mixture was allowed to stand for one hour. The reaction mixture was washed with an aqueous 5% sodium hydrogen carbonate solution, dried, and then the solvent thereof was distilled off. The residue was purified by silica gel chromatography using chloroform as the eluent and further recrystallized from aqueous ethanol to provide 0.2 g of 6-(3,5-di-tert-butyl-4-hydroxyphenyl)-2,3-dihydroimidazo[2,1-b]thiazole 1,1-dioxide.

Workup

  1. waitto stand for one hour
  2. washThe reaction mixture was washed with an aqueous 5% sodium hydrogen carbonate solution
  3. customdried
  4. distillationthe solvent thereof was distilled off
  5. customThe residue was purified by silica gel chromatography
  6. customfurther recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-f4d693e2fcf943789c62b0666a2bd331
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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