Potassium Carbonate → HCID 57750149, compound

HRID 504594Notes

Reaction equation

HRID 504594 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].Cl[CH2:12][S:13][CH3:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:12][S:13][CH3:14])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 16916Chloromethyl methyl sulfide

Product 1

HCID 57750149HCID 57750149, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5-chloro-2-hydroxy-benzaldehyde (15.6 g, 0.1 mol), chloro-methylsulfanyl-methane (9.6 g, 0.1 mol), K2CO3 (14 g, 0.1 mol) and KI (1 g, 0.006 mol) in DMF (70 mL) was heated at 70° C. for 2 h. After cooled to the room temperature, the mixture was poured into ice water. The aqueous phase was extracted with diethyl ether. The combined organic layers were washed with NaOH solution (1 N), dried over anhydrous Na2SO4 and concentrated to give the title compound as a yellow oil (14.2 g).

Workup

  1. temperatureAfter cooled to the room temperature
  2. extractionThe aqueous phase was extracted with diethyl ether
  3. washThe combined organic layers were washed with NaOH solution (1 N)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1b544b84f4b54f65bdc449400d976c12
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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