Dimethylformamide → Bis{4-[(phenylmethyl)oxy]phenyl}disulfide

HRID 130431

Reaction equation

HRID 130431 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[C:7]1(O)[CH:12]=[CH:11][C:10]([S:13][S:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1.CN(C)C=O.[CH2:28](Cl)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CO.O>[C:29]1([CH2:28][O:21][C:18]2[CH:19]=[CH:20][C:15]([S:14][S:13][C:10]3[CH:11]=[CH:12][C:7]([O:4][CH2:1][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[CH:8][CH:9]=3)=[CH:16][CH:17]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 2806654-[(4-Hydroxyphenyl)disulfanyl]phenol

Product 1

HCID 54075991Bis{4-[(phenylmethyl)oxy]phenyl}disulfide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To solid potassium carbonate (11.59 g, 83.89 mmol) was added 4,4′-dithiodiphenol (7.00 g, 27.96 mmol), as a solid under argon, followed by N,N-dimethylformamide (130 ml). The stirred suspension was then heated to 80° C. over 2.25 h. Benzyl chloride (7.24 ml, 62.91 mmol) was then added over 2-3 minutes and the mixture stirred at 80° C. overnight. The mixture was then allowed to cool slowly to room temperature over the weekend. The resulting mixture was then poured into water (800 ml) and extracted with dichloromethane (3×250 ml). The organic extracts were combined and dried over sodium sulfate, filtered and evaporated to give a pale yellow solid which was tritureated with hot methanol (80 ml) which was allowed to cool slowly overnight to afford the title compound (D47). 1H-NMR (CDCl3) d 7.43-7.33 (14H, m), 6.90 (4H, dd, J 6.8 Hz, 2.0 Hz), 5.05 (4H, s).

Workup

  1. temperatureto cool slowly to room temperature over the weekend
  2. extractionextracted with dichloromethane (3×250 ml)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a pale yellow solid which
  7. temperatureto cool slowly overnight

Sources & evidence

ORD record
ord-c915a03f01c64507a69c749c000acad5
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Linked notes

Loading…