m-Chloroperbenzoic acid → 8-Chloro-3-cyanodibenzo[b,f]thiepin-5,5-dioxide

HRID 485446Notes

Reaction equation

HRID 485446 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:18]=1.ClC1C=CC=C(C(OO)=O)C=1.[OH-:30].[Ca+2].[OH-:32]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11](=[O:32])(=[O:30])[C:10]3[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:18]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 131518898-Chloro-3-cyanodibenzo[b,f]thiepin

Product 1

HCID 131518908-Chloro-3-cyanodibenzo[b,f]thiepin-5,5-dioxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

400 Mg. 8-chloro-3-cyanodibenzo[b,f]-thiepin is dissolved in 30 cc. chloroform and 2 g. m-chloroperbenzoic acid added, and the solution stirred for 24 hours. 5 G. calcium hydroxide is added, the mixture stirred for five minutes and filtered through celite. The organic filtrate is evaporated to dryness and the residue chromatographed on silica gel and eluted with 5% ethyl acetate/benzene mixture to yield 339 mg. (76%) pure sulfone, m.p. 228°-230° C.

Workup

  1. stirringthe mixture stirred for five minutes
  2. filtrationfiltered through celite
  3. customThe organic filtrate is evaporated to dryness
  4. customthe residue chromatographed on silica gel
  5. washeluted with 5% ethyl acetate/benzene mixture
  6. customto yield 339 mg

Sources & evidence

ORD record
ord-0b15d785330f471ab75bd9f49cdb54b9
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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