Dimethylformamide → Dimethyl 2,2'-dithiobisbenzoate

HRID 600168

Reaction equation

HRID 600168 reaction equation
C(O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][S:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].CN(C)[CH:23]=[O:24].[CH2:26](N(CC)CC)C.[C:33]([O-:36])([O-])=O.[K+].[K+]>O=S(Cl)Cl.C(Cl)(Cl)Cl.O.CO>[CH3:33][O:36][C:23](=[O:24])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][C:3]=1[S:8][S:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([O:14][CH3:26])=[O:13]

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 8409Dithiodibenzoic acidHCID 8471TriethylamineHCID 11430Potassium Carbonate

Product 1

HCID 79574Dimethyl 2,2'-dithiobisbenzoateYield 50%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 24386Thionyl ChlorideSolvent

Procedure

25 g (81.6 mmol) of dithiodibenzoic acid is refluxed in 60 ml of SOCl2 and 1.5 ml of dimethylformamide (DMF) for 3 hrs. Then the excess of SOCl2 is distilled off, and the residue is dissolved in CHCl3 and added dropwise to a solution of methanol (50 ml) and triethylamine (0.204 mol) in CHCl3 (300 l). After standing over night the reaction mixture is shaked with water and saturated K2CO3 solution. After drying the organic layer the solvent is evaporated and methanol is added to the residue (oil). 13.6 g (50%) of solid product is obtained.

Workup

  1. distillationThen the excess of SOCl2 is distilled off
  2. dissolutionthe residue is dissolved in CHCl3
  3. waitAfter standing over night
  4. customAfter drying the organic layer the solvent
  5. customis evaporated
  6. additionmethanol is added to the residue (oil)

Sources & evidence

ORD record
ord-cad53b8c9b884337997cc19785bc4fe7
Source dataset
uspto-grants-2011_03
Patent number
US07901867B2

Linked notes

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