Hydrochloric Acid → HCID 57750141, compound

HRID 504600Notes

Reaction equation

HRID 504600 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C([O-])([O-])=O.[K+].[K+].[C:17]([NH:21][S:22]([CH2:25]Cl)(=[O:24])=[O:23])([CH3:20])([CH3:19])[CH3:18].Cl>CN(C=O)C>[C:17]([NH:21][S:22]([CH2:25][O:10][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=1[CH:7]=[O:8])(=[O:24])=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 282245115719-94-3

Product 1

HCID 57750141HCID 57750141, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-chloro-2-hydroxy-benzaldehyde (13.9 g, 89.2 mmol), K2CO3 (24.6 g, 178.3 mmol) and N-tert-butyl-C-chloro-methanesulfonamide (16.5 g, 89.2 mmol) in DMF (20 mL) was heated at 60° C. overnight. After cooled to room temperature, the mixture was neutralized by addition of aqueous HCl solution and extracted with ethyl acetate. The organic phase was washed with water, brine, dried over anhydrous Na2SO4 and concentrated to give the crude product. The crude product was washed with diethyl ether to give the title compound (13.5 g).

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give the crude product
  7. washThe crude product was washed with diethyl ether

Sources & evidence

ORD record
ord-8301fc0c483e47f9bdb14201eee753de
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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