m-Chloroperbenzoic acid → 3-Cyanodibenzo[b,f]thiepin 5-oxide

HRID 1074977Notes

Reaction equation

HRID 1074977 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[S:8][C:7]=2[CH:17]=1)#[N:2].ClC1C=CC=C(C(OO)=[O:26])C=1.[OH-].[Ca+2].[OH-]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[S:8](=[O:26])[C:7]=2[CH:17]=1)#[N:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 13490383HCID 13490383, compound

Product 1

HCID 131518733-Cyanodibenzo[b,f]thiepin 5-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 G. 3-cyanodibenzo[b,f]thiepin (0.021 mole) are dissolved in 300 cc. methylene chloride and 3.45 g. m-chloroperbenzoic acid (0.020 mole) are added in portions. The solution is stirred for two hours at room temperature, then excess calcium hydroxide is added. The mixture is stirred for a few minutes and filtered through celite, the filtrate is evaporated down and the residue chromatographed on silica gel, eluting with a 50:50 mixture of chloroform and benzene. A small amount of starting material is recovered, and the yield of sulfoxide is 4.92 g. (92%), light yellow solid, m.p. 220° C.-222° C.

Workup

  1. stirringThe mixture is stirred for a few minutes
  2. filtrationfiltered through celite
  3. customthe filtrate is evaporated down
  4. customthe residue chromatographed on silica gel
  5. washeluting with a 50:50 mixture of chloroform and benzene
  6. customA small amount of starting material is recovered

Sources & evidence

ORD record
ord-4d45b85dd4294790ae3baf9d76f437c5
Source dataset
uspto-grants-1983_07
Patent number
US04394515

Reaction notes

Loading…