Carbon Disulfide → HCID 178441374, compound

HRID 344970Notes

Reaction equation

HRID 344970 reaction equation
[CH3:1][C:2]1([C:7]([CH3:10])([CH3:9])[CH3:8])[NH:6][CH2:5][CH2:4][O:3]1.[OH-].[Na+].[C:13](=[S:15])=[S:14].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[CH2:16]([SH:14]=[C:13]([N:6]1[CH2:5][CH2:4][O:3][C:2]1([CH3:1])[C:7]([CH3:10])([CH3:9])[CH3:8])[SH:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6348Carbon Disulfide2×HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 12801340HCID 12801340, compound

Product 1

HCID 178441374HCID 178441374, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

28.6 g (0.2 mole) of 2-methyl-2-(tert.butyl)-oxazolidine and 8.0 g (0.2 mole) of sodium hydroxide dissolved in 80 cm3 of water were placed into a round-bottom flask equipped with a reflux condenser, a thermometer, a dropping funnel and a stirrer. With continuous stirring and cooling, 15.2 g (12.05 cm3, 0.2 mole) of carbon disulphide was introduced dropwise while the temperature was not allowed to rise above 20° C. As the introduction of carbon disulphide had been completed, the mixture was continued to stir at room temperature for 2 hours. Under cooling and stirring, 25.2 g (22.96 cm3, 0.2 mole) of benzylchloride was added dropwise below 10° C. Stirring was continued for 2 hours after the introduction had been completed. The organic layer was separated from the aqueous one and the latter was extracted by chloroform. The unified organic phases were washed with water, dried above sodium sulphate, and then the solvent was distilled off. Yield: 36.8 g (61.8%).

Workup

  1. customwere placed into a round-bottom flask
  2. customequipped with a reflux condenser
  3. temperaturecooling
  4. customto rise above 20° C
  5. stirringto stir at room temperature for 2 hours
  6. temperatureUnder cooling
  7. stirringstirring
  8. stirringStirring
  9. customThe organic layer was separated from the aqueous one
  10. extractionthe latter was extracted by chloroform
  11. washThe unified organic phases were washed with water
  12. dry with materialdried above sodium sulphate
  13. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-2ffc6c6550e247fbab32d192c3c2238a
Source dataset
uspto-grants-1991_10
Patent number
US05055125

Reaction notes

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