Potassium Iodide → HCID 21481149, compound

HRID 435685Notes

Reaction equation

HRID 435685 reaction equation
[I:1][C:2]1[CH:22]=[CH:21][C:5]2[S:6][C:7]3[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=3[CH:9]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[CH2:10][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:32][CH2:33][N:34]1[CH2:38][CH2:37][O:36][C:35]1=[O:39]>C(Cl)(Cl)Cl.O.C1(C)C=CC=CC=1>[I:1][C:2]1[CH:22]=[CH:21][C:5]2[S:6][C:7]3[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=3[CH:9]([N:11]3[CH2:12][CH2:13][N:14]([CH2:32][CH2:33][N:34]4[CH2:38][CH2:37][O:36][C:35]4=[O:39])[CH2:15][CH2:16]3)[CH2:10][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 756333-(2-Chloroethyl)-1,3-oxazolidin-2-oneHCID 21456041HCID 21456041, compound

Product 1

HCID 21481149HCID 21481149, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

5.9 g of 1-(10,11-dihydro-2-iodo-dibenzo[b,f]thiepin-10-yl)-piperazine are treated, together with 3.3 g of powdered potassium carbonate, 0.07 g of potassium iodide and 40 ml of toluene, with 4.35 g of N-(β-chloroethyl)-oxazolidinone and the mixture is heated under reflux for 27 hours. The mixture is then poured on to water and diluted with chloroform. The organic phase is extracted with 2-N hydrochloric acid. The aqueous phase is made alkaline with sodium hydroxide and extracted with chloroform. The organic phase is dried over magnesium sulphate and concentrated under reduced pressure. The residue is chromatographed over aluminium oxide. There is obtained 3-[ 2-[4-(10,11-dihydro-2-iodo-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl ]-2-oxazolidinone which is converted into the maleate by treatment with maleic acid. The maleate melts at 176°-177° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 27 hours
  3. extractionThe organic phase is extracted with 2-N hydrochloric acid
  4. extractionextracted with chloroform
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is chromatographed over aluminium oxide

Sources & evidence

ORD record
ord-45841207dab045c59e18bf7340752796
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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