Water → HCID 50907591, compound

HRID 1913846Notes

Reaction equation

HRID 1913846 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9]([OH:12])(=[O:11])=[O:10].[Na].[CH3:14][C:15](N(C)C)=O.[OH2:20]>C(O)C.[Cu]>[Cl:8][C:5]1[CH:4]=[C:3]([S:9]([OH:12])(=[O:11])=[O:10])[C:2]([C:2]2[C:3]([S:9]([OH:11])(=[O:10])=[O:20])=[CH:4][C:5]([Cl:8])=[CH:14][CH:15]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 31374DimethylacetamideHCID 66616Benzenesulfonic acid, 2,5-dichloro-HCID 5360545Sodium2×

Product 1

HCID 50907591HCID 50907591, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

Inside a glove box, a 300 mL round-bottom flask equipped with a reflux condenser, stirring bar, and gas inlet was charged with anhydrous 2,5-dichlorobenzenesulfonic acid, sodium salt (24.9 g, 0.1 moles), activated copper bronze (12.7 g, 0.2 moles), and DMAc (100 mL). The mixture was heated to 150° C. overnight under nitrogen. The mixture was poured into water (1 L) and the solid removed by vacuum filtration. The filtrate was treated with sufficient sodium carbonate to precipitate residual copper salts, which were removed by vacuum filtration. The solution was evaporated and the residue dried at 150° C. under vacuum. The solids (29.75 g) were dissolved in a mixture of ethanol and water, acidified with acetic acid, filtered, and concentrated to give an oil. The oil was dissolved in ethanol (100 mL) and allowed to set overnight to give a copious white solid, which was collected by vacuum filtration and washed twice with ethanol. The solids were recrystallized twice from ethanol to give 10.05 g (47% yield) of 4,4′-dichlorobiphenyl-2,2′-disulfonic acid, sodium salt. 1H NMR (DMSO-d6): 7.30 (d, 8.2 Hz, 2H), 7.34 (dd, 8.2, 2.3 Hz, 2H), 7.82 (d, 2.2 Hz, 2H).

Workup

  1. customInside a glove box, a 300 mL round-bottom flask equipped with a reflux condenser
  2. customthe solid removed by vacuum filtration
  3. additionThe filtrate was treated with sufficient sodium carbonate
  4. customto precipitate residual copper salts, which
  5. customwere removed by vacuum filtration
  6. customThe solution was evaporated
  7. customthe residue dried at 150° C. under vacuum
  8. dissolutionThe solids (29.75 g) were dissolved in a mixture of ethanol and water
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give an oil
  12. customto give a copious white solid, which
  13. filtrationwas collected by vacuum filtration
  14. washwashed twice with ethanol
  15. customThe solids were recrystallized twice from ethanol

Sources & evidence

ORD record
ord-d8018c515f38478fac604c3fa960ec03
Source dataset
uspto-grants-2013_12
Patent number
US08609804B2

Reaction notes

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