m-Chloroperbenzoic acid → 3-Cyano-8-nitrodibenzo[b,f]thiepin-5,5-dioxide

HRID 485438Notes

Reaction equation

HRID 485438 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:9]=3[S:8][C:7]=2[CH:20]=1)#[N:2].ClC1C=CC=C(C(OO)=O)C=1.[OH-:32].[Ca+2].[OH-:34]>C(Cl)(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:9]=3[S:8](=[O:34])(=[O:32])[C:7]=2[CH:20]=1)#[N:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 131518793-Cyano-8-nitrodibenzo[b,f]thiepin

Product 1

HCID 202702143-Cyano-8-nitrodibenzo[b,f]thiepin-5,5-dioxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2 G. 3-cyano-8-nitrodibenzo[b,f]thiepin is dissolved in 600 cc. chloroform and 12 g. m-chloroperbenzoic acid added. The solution is stirred for 24 hours. Excess powdered calcium hydroxide is added, the mixture filtered through celite, the filtrate evaporated to dryness and the residue chromatographed on silica gel. Elution with 5% ethyl acetate in benzene afforded 1.36 g. (61%) of pure sulfone.

Workup

  1. additionis added
  2. filtrationthe mixture filtered through celite
  3. customthe filtrate evaporated to dryness
  4. customthe residue chromatographed on silica gel
  5. washElution with 5% ethyl acetate in benzene
  6. customafforded 1.36 g

Sources & evidence

ORD record
ord-24e50a0680304f97a73d4bb42a8af988
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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