Potassium Carbonate → 2-chloro-11H-dibenzo[b,f][1,4]oxathiepine

HRID 1388546Notes

Reaction equation

HRID 1388546 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:9]=1)[CH2:7]Br.C(=O)([O-])[O-].[K+].[K+].[OH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[SH:24]>CN(C)C=O.[Cu]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[S:24][CH2:7][C:6]=2[CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 70718Phenol, o-mercapto-(6CI,7CI,8CI)HCID 98623842-(Bromomethyl)-4-chloro-1-iodobenzene

Product 1

HCID 129309632-chloro-11H-dibenzo[b,f][1,4]oxathiepineYield 45.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 125.6 g of 5-chloro-2-iodobenzyl bromide in 500 ml of dimethylformamide is added to a mixture of 640 ml of dimethylformamide, 52.4 g of potassium carbonate and 47.8 g of 2-hydroxythiophenol (R. Leuckart, J.Prakt.Chem. /2/ 41, 192, 1890). Then, the mixture is stirred for 1 hour at room temperature, treated with 57 g. of potassium carbonate and 4.5 g of copper and is refluxed for 6 hours. Dimethylformamide is distilled off under reduced pressure, the residue diluted with water and shaken with benzene. After filtration, the benzene layer is separated, washed with water, dried with potassium carbonate and evaporated. By distillation of the residue there are obtained 42.5 g (45%) of 2-chloro-11H-dibenz(b.f)-1,4-oxathiepin with a b.p. of 148°-168° C./85 Pa and m.p. of 66.76° C. The pure product is obtained by crystallization from methanol and melts at 78°-79° C.

Workup

  1. additiontreated with 57 g
  2. distillationDimethylformamide is distilled off under reduced pressure
  3. additionthe residue diluted with water
  4. stirringshaken with benzene
  5. filtrationAfter filtration
  6. customthe benzene layer is separated
  7. washwashed with water
  8. dry with materialdried with potassium carbonate
  9. customevaporated
  10. distillationBy distillation of the residue there

Sources & evidence

ORD record
ord-af8a867f91d0437c9d3c138093d805b0
Source dataset
uspto-grants-1984_02
Patent number
US04431808

Reaction notes

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