Potassium Hydroxide → HCID 19604516, compound

HRID 1604734Notes

Reaction equation

HRID 1604734 reaction equation
[OH-].[K+].[C:3]1([CH2:9][CH2:10][CH2:11][SH:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:14]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:15]=1[CH:16]=[O:17]>CN(C=O)C>[C:3]1([CH2:9][CH2:10][CH2:11][S:12][C:14]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:15]=2[CH:16]=[O:17])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 729332-Chloro-5-nitrobenzaldehydeHCID 905963-Phenylpropane-1-thiol

Product 1

HCID 19604516HCID 19604516, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a reaction mixture of DMF (40 mL), potassium hydroxide (1.45 g, 25.9 mmol), and 3-phenylpropyl mercaptan (3.28 g, 21.6 mmol), was added 2-chloro-5-nitrobenzaldehyde (4.00 g, 21.6 mmol). The resulting mixture was heated at 100° C. for 45 minutes. The mixture was cooled, poured onto ice-water (350 mL) and allowed to stand at room temperature for 48 hours. A yellow semi-solid which formed was collected and dissolved in ethyl acetate (100 mL), dried over Na2SO4, and filtered. The solvent removed by evaporation to give a dark yellow gum, 6.71 g.1H NMR (CDCl3): d, 10.27 (s,1H,CHO). MS (DCl): 302 (MH+). The crude product was carried on without further purification in example 34. C16H15NO3S.

Workup

  1. temperatureThe mixture was cooled
  2. additionpoured onto ice-water (350 mL)
  3. customA yellow semi-solid which formed
  4. customwas collected
  5. dissolutiondissolved in ethyl acetate (100 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customThe solvent removed by evaporation
  9. customto give a dark yellow gum, 6.71 g
  10. customThe crude product was carried on without further purification in example 34

Sources & evidence

ORD record
ord-58fe8dc620d44ed6bb69b4870689d0e8
Source dataset
uspto-grants-1999_11
Patent number
US05994563

Reaction notes

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