m-Chloroperbenzoic acid → HCID 13151865, compound

HRID 485433Notes

Reaction equation

HRID 485433 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:12](=[O:13])[CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[S:8][C:7]=2[CH:18]=1)#[N:2].ClC1C=CC=C(C(OO)=[O:27])C=1>C(Cl)Cl.[OH-].[Ca+2].[OH-]>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:12](=[O:13])[CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[S:8](=[O:27])[C:7]=2[CH:18]=1)#[N:2]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13151854HCID 13151854, compound

Product 1

HCID 13151865HCID 13151865, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6093208Calcium HydroxideSolvent

Procedure

1.63 G. 3-cyano-10,11-dihydro-11-oxodibenzo[b,f]thiepin is dissolved in 100 cc. methylene chloride and 1.12 g. m-chloroperbenzoic acid is added and the solution stirred for one hour at room temperature. The reaction mixture is diluted with methylene chloride, excess powdered calcium hydroxide is added, and 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 a 1:1 mixture of benzene: chloroform to yield 937 mg. (54%) of the desired pure sulfoxide, m.p. 219°-221° C.

Workup

  1. additionis added
  2. stirringthe mixture stirred for five minutes
  3. filtrationfiltered through celite
  4. customThe organic filtrate is evaporated to dryness
  5. customthe residue chromatographed on silica gel
  6. washeluted with a 1:1 mixture of benzene
  7. customchloroform to yield 937 mg

Sources & evidence

ORD record
ord-82f70c46c95f4797b66356cab7c21f4a
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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