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

HRID 1075007Notes

Reaction equation

HRID 1075007 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-60b89d9ebb8e4f199da891dadebcf87d
Source dataset
uspto-grants-1983_07
Patent number
US04394515

Reaction notes

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