Sodium Bicarbonate → 3-[2-[4-(8-Chloro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl]-2-oxazolidinone

HRID 1075879Notes

Reaction equation

HRID 1075879 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=3[CH2:8][C:7](=O)[C:6]=2[CH:18]=1.[N:19]1([CH2:25][CH2:26][N:27]2[CH2:31][CH2:30][O:29][C:28]2=[O:32])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(=O)(O)[O-].[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=3[CH:8]=[C:7]([N:22]3[CH2:23][CH2:24][N:19]([CH2:25][CH2:26][N:27]4[CH2:31][CH2:30][O:29][C:28]4=[O:32])[CH2:20][CH2:21]3)[C:6]=2[CH:18]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 122755453-[2-(1-Piperazinyl)ethyl]-2-oxazolidinoneHCID 214160928-chloro-2-methyl-dibenzo[b,f]thiepin-10(11H)-one

Product 1

HCID 214160983-[2-[4-(8-Chloro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl]-2-oxazolidinone

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 241BenzeneSolvent2×

Conditions

Temperature
40 °C

Procedure

27.4 G. of 8-chloro-2-methyl-dibenzo[b,f]thiepin-10(11H)-one, 400 ml. of absolute benzene and 40 g. of 3-[2-(1-piperazinyl)-ethyl]-2-oxazolidinone are stirred under an atmosphere of argon at 20°C. To the mixture, there are added dropwise over a period of 60 minutes, 9.3 ml. of titanium tetrachloride in 200 ml. of absolute benzene. The mixture is subsequently heated at reflux for 3.5 hours and, after cooling to about 40°C., poured on to a saturated, aqueous sodium bicarbonate solution and stirred for an additional 30 minutes. The suspension obtained is filtered and the benzene phase separated. The aqueous phase is back-extracted with 100 ml. of benzene. The combined benzene extracts are washed with water, dried over magnesium sulfate, filtered and evaporated. By recrystallization from acetonitrile, there is recovered from the residue still unchanged 8-chloro-2-methyldibenzo[b,f]thiepin-10(11H)-one. The mother liquor is evaporated and the residue recrystallized from benzene, whereby there is obtained 3-{2-[4-(8-chloro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone which melts at 194°-196°C.

Workup

  1. additionTo the mixture, there are added dropwise over a period of 60 minutes
  2. temperatureThe mixture is subsequently heated
  3. temperatureat reflux for 3.5 hours
  4. customThe suspension obtained
  5. filtrationis filtered
  6. customthe benzene phase separated
  7. extractionThe aqueous phase is back-extracted with 100 ml
  8. washThe combined benzene extracts are washed with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customBy recrystallization from acetonitrile, there
  13. customis recovered from the residue still unchanged 8-chloro-2-methyldibenzo[b,f]thiepin-10(11H)-one
  14. customThe mother liquor is evaporated
  15. customthe residue recrystallized from benzene

Sources & evidence

ORD record
ord-7a18dfa68e844cb4a780571d4a48cd67
Source dataset
uspto-grants-1976_05
Patent number
US03954764

Reaction notes

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