Diethylamine → HCID 23106069, compound

HRID 2251405Notes

Reaction equation

HRID 2251405 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].Cl[S:7][S:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][S:16]Cl)=[CH:11][CH:10]=1>ClCCCl>[CH2:1]([N:3]([S:7][S:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][S:16][N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:11][CH:10]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 86602998HCID 86602998, compound

Product 1

HCID 23106069HCID 23106069, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

25.0 ml (190 mmol) of diethylamine are used as initial charge in 150 ml of 1,2-dichloroethane in an inertized three-necked flask with dropping funnel, reflux condenser with hose coupling at its upper end, a tap with hose coupling and a Teflon stirrer bar, in a countercurrent of argon. 10.6 g (38.6 mmol) of 1,4-bis(chlorodisulphanyl)benzene in 50 ml of 1,2-dichloroethane are then slowly added dropwise, with stirring. The reaction mixture is stirred at room temperature for 4 hours. The resultant salt is filtered off, and the organic phase is washed three times with water and dried over sodium sulphate. After removal of the solvent on a rotary evaporator and drying in the vacuum generated by a rotary-vane pump, 1,4-bis(diethylaminodisulphanyl)benzene precipitates in the form of a yellow oil. The crude yield is 11.9 g (89%). Elemental analysis was carried out on the crude product.

Workup

  1. temperaturereflux condenser with hose coupling at its upper end
  2. stirringThe reaction mixture is stirred at room temperature for 4 hours
  3. filtrationThe resultant salt is filtered off
  4. washthe organic phase is washed three times with water
  5. dry with materialdried over sodium sulphate
  6. customAfter removal of the solvent
  7. customon a rotary evaporator
  8. customdrying in the vacuum
  9. customprecipitates in the form of a yellow oil

Sources & evidence

ORD record
ord-956a71fd9c284aafa0a9da9f9a25e828
Source dataset
uspto-grants-2008_01
Patent number
US07319124B2

Reaction notes

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