Sodium Hydroxide → HCID 59846261, compound

HRID 1697066Notes

Reaction equation

HRID 1697066 reaction equation
[OH-].[Na+].[CH3:3][C:4]1([CH3:22])[O:8][CH:7]([CH2:9][NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH2:6][O:5]1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:32])[CH3:31])=[C:26]([NH:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:25]=1>CO>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:32])/[CH:31]=[CH:20]/[C:17]2[CH:18]=[CH:19][C:14]([S:11]([NH:10][CH2:9][CH:7]3[CH2:6][O:5][C:4]([CH3:22])([CH3:3])[O:8]3)(=[O:13])=[O:12])=[CH:15][CH:16]=2)=[C:26]([NH:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:25]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 598461761-(4-Chloro-2-phenylaminophenyl)ethanoneHCID 59846254HCID 59846254, compound

Product 1

HCID 59846261HCID 59846261, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaOH (2 M aq, 0.91 mL, 1.8 mmol) was added to a solution of N-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-formyl-benzenesulfonamide (305 mg, 1 mmol) and 1-(4-chloro-2-phenylamino-phenyl)-ethanone (250 mg, 1 mmol) in MeOH (10 mL), and the resulting mixture stirred at RT overnight. A second aliquot of NaOH (2 M aq, 0.1 mL) was added, and the reaction mixture was again stirred at RT overnight. The resulting mixture was evaporated under reduced pressure, and the crude residue partitioned between water and EtOAc. The organic layer was separated, and the aqueous layer was extracted twice with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to give an oil. The crude residue was purified twice by flash chromatography (EtOAc/hexane) to give 4-[(E)-3-(4-chloro-2-phenylamino-phenyl)-3-oxo-propenyl]-N-(2,2-dimethyl[1,3]dioxolan-4-ylmethyl)-benzenesulfonamide (70 mg).

Workup

  1. stirringthe reaction mixture was again stirred at RT overnight
  2. customThe resulting mixture was evaporated under reduced pressure
  3. customthe crude residue partitioned between water and EtOAc
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted twice with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto give an oil
  11. customThe crude residue was purified twice by flash chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-f3a88466a15f4179903bb319ea9664e2
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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